Lithium hydroxide, monohydrate → HCID 59511427, compound

HRID 1157590Notes

Reaction equation

HRID 1157590 reaction equation
FC(F)(F)C([N:5]([CH2:44][CH2:45][S:46]([CH3:49])(=[O:48])=[O:47])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]2[N:19]=[C:18]([C:20]3[C:21]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([NH:35][C:36](=[O:43])[CH2:37][C:38]5[S:39][CH:40]=[CH:41][CH:42]=5)[CH:30]=4)=[N:22][N:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=34)[CH:17]=[CH:16][N:15]=2)[CH:8]=1)=O.O[Li].O>C1COCC1.O.CCOC(C)=O>[CH3:49][S:46]([CH2:45][CH2:44][NH:5][CH2:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[N:19]=[C:18]([C:20]3[C:21]([C:29]4[CH:30]=[C:31]([NH:35][C:36](=[O:43])[CH2:37][C:38]5[S:39][CH:40]=[CH:41][CH:42]=5)[CH:32]=[CH:33][CH:34]=4)=[N:22][N:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=34)[CH:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1)(=[O:47])=[O:48]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 577372392,2,2-Trifluoro-N-[2-(methylsulfonyl)ethyl]-N-[(3-{[4-(2-{3-[(2-thienylacetyl)amino]phenyl}pyrazolo[1,5-a]pyridin-3-yl)-2-pyrimidinyl]amino}phenyl)methyl]acetamide

Product 1

HCID 59511427HCID 59511427, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2,2,2-trifluoro-N-[2-(methylsulfonyl)ethyl]-N-[(3-{[4-(2-{3-[(2-thienylacetyl)amino]phenyl}pyrazolo[1,5-a]pyridin-3-yl)-2-pyrimidinyl]amino}phenyl)methyl]acetamide (79 mg, 0.11 mmol) in THF (3 mL) was added LiOH hydrate (10 mg, 0.21 mmol) in water (0.5 mL). The solution was heated to 50° C. for 2 h, and then diluted with EtOAc, washed with 1N Na2CO3, dried over Na2SO4, and concentrated to generate the title compound in 62% yield. 1H NMR (400 MHz, d6-DMSO) δ 10.36 (s, 1H), 9.55 (s, 1H), 8.84 (d, J=6.8 Hz, 1H), 8.52 (d, J=8.9 Hz, 1H), 8.24 (d, J=5.4 Hz, 1H), 7.90 (s, 1H), 7.74-7.76 (m, 2H), 7.59 (d, J=8.1 Hz, 1H), 7.38-7.50 (m, 2H), 7.28 (d, J=7.7 Hz, 1H), 7.20 (t, J=7.8 Hz, 1H), 7.13 (t, J=6.8 Hz, 1H), 6.92-6.98 (m, 3H), 6.44-6.51 (m, 2H), 3.88 (s, 2H), 3.66 (s, 2H), 3.23 (t, J=6.3 Hz, 2H), 3.01 (s, 3H), 2.91 (t, J=6.1 Hz). ES-LC/MS m/z=638 [M+H]+.

Workup

  1. washwashed with 1N Na2CO3
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9c09ada226764121896c2e9887ec4a32
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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