Methanol → HCID 46840924, compound

HRID 1896580Notes

Reaction equation

HRID 1896580 reaction equation
[N:1]1([C:10]2[CH:51]=[CH:50][C:13]([O:14][CH2:15][CH2:16][CH2:17][C:18]3[S:22][C:21]([C:23]4[CH:32]=[C:31]5[C:26]([CH2:27][CH2:28][CH2:29][N:30]5[C:33](=[O:44])[NH:34][C:35]5[S:36][C:37]6[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=6[N:39]=5)=[CH:25][CH:24]=4)=[N:20][C:19]=3[C:45]([O:47]CC)=[O:46])=[CH:12][CH:11]=2)[C:5]2=[N:6][CH:7]=[N:8][CH:9]=[C:4]2[CH:3]=[N:2]1.CO.C1COCC1.[Li+].[OH-]>O>[N:1]1([C:10]2[CH:11]=[CH:12][C:13]([O:14][CH2:15][CH2:16][CH2:17][C:18]3[S:22][C:21]([C:23]4[CH:32]=[C:31]5[C:26]([CH2:27][CH2:28][CH2:29][N:30]5[C:33](=[O:44])[NH:34][C:35]5[S:36][C:37]6[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=6[N:39]=5)=[CH:25][CH:24]=4)=[N:20][C:19]=3[C:45]([OH:47])=[O:46])=[CH:50][CH:51]=2)[C:5]2=[N:6][CH:7]=[N:8][CH:9]=[C:4]2[CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 59418777HCID 59418777, compound

Product 1

HCID 46840924HCID 46840924, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

The title compound 5-(3-(4-(1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenoxy)propyl)-2-(1-(benzo[d]thiazol-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl)thiazole-4-carboxylic acid (23) was prepared by the following procedure: To ethyl 5-(3-(4-(1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenoxy)propyl)-2-(1-(benzo[d]thiazol-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl)thiazole-4-carboxylate (23I) (120 mg, 0.17 mmol) was added MeOH and THF. LiOH (20 mg, 0.85 mmol) was dissolved in water and added to the reaction mixture. The reaction mixture was stirred and heated at 60° C. for two hours. The reaction was cooled and put in refrigerator overnight. The precipitate was transferred to a centrifuge tube and centrifuged down at 17,000 RPM. The precipitate was washed water. Then the precipitate was added to acetonitrile and water and lyophilized to give 69 mg (59%) of the desired product 5-(3-(4-(1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenoxy)propyl)-2-(1-(benzo[d]thiazol-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl)thiazole-4-carboxylic acid (23): 1H NMR (400 MHz, DMSO) δ 9.44 (s, 1H), 9.10 (s, 1H), 8.61 (s, 1H), 8.04 (d, J=8.7, 2H), 7.66 (s, 1H), 7.45 (d, J=34.2, 2H), 7.20 (t, J=18.3, 5H), 4.12 (s, 3H), 3.95 (s, 3H), 2.79 (s, 2H), 2.16 (s, 3H), 1.89 (s, 2H), −0.00 (s, 3H).

Workup

  1. customThe title compound 5-(3-(4-(1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenoxy)propyl)-2-(1-(benzo[d]thiazol-2-ylcarbamoyl)-1,2,3,4-tetrahydroquinolin-7-yl)thiazole-4-carboxylic acid (23) was prepared by the following procedure
  2. additionadded to the reaction mixture
  3. temperatureThe reaction was cooled
  4. customput in refrigerator overnight
  5. customThe precipitate was transferred to a centrifuge tube
  6. washThe precipitate was washed water
  7. additionThen the precipitate was added to acetonitrile and water

Sources & evidence

ORD record
ord-5a899df6b6684b678381e675ea9c8d2e
Source dataset
uspto-grants-2013_08
Patent number
US08518970B2

Reaction notes

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