Lithium Hydroxide → HCID 68682530, compound

HRID 1157562Notes

Reaction equation

HRID 1157562 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]2[C:24]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32]4[CH:41]=C5C(CCCN5C(=O)C(F)(F)F)=[CH:34][CH:33]=4)[N:26]=3)=[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][N:18]3[N:17]=2)[CH:11]=1)=[O:8].[Li+].[OH-]>CO>[CH2:19]1[C:20]2[C:21](=[CH:34][CH:33]=[C:32]([NH:31][C:27]3[N:26]=[C:25]([C:24]4[C:16]([C:12]5[CH:11]=[C:10]([NH:9][C:7](=[O:8])[CH2:6][C:2]6[S:1][CH:5]=[CH:4][CH:3]=6)[CH:15]=[CH:14][CH:13]=5)=[N:17][N:18]5[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=45)[CH:30]=[CH:29][N:28]=3)[CH:41]=2)[CH2:22][CH2:23][NH:18]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86631084HCID 86631084, compound

Product 1

HCID 68682530HCID 68682530, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(2-thienyl)-N-{3-[3-(2-{[1-(trifluoroacetyl)-1,2,3,4-tetrahydro-7-quinolinyl]amino}-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}acetamide (0.075 g, 0.11 mmol) and LiOH (50 mg, 1.2 mmol) in MeOH (10 mL) was stirred for 30 min. The reaction mixture was evaporated down and the crude taken up in DCM and washed with brine. Purification via column chromatography using a 0-30% gradient of EtOAc/MeOH generated the product as a yellow solid in 42% yield. 1H NMR (400 MHz, d6-DMSO): δ 10.36 (s, 1H), 9.41 (s, 1H), 8.83 (d, 1H), 8.48 (d, 1H), 8.22 (d, 1H), 7.89 (s, 1H), 7.75 (d, 2H), 7.43 (m, 5H), 7.28 (d, 1H), 7.12 (t, 1H), 6.97 (m, 3H), 6.44 (d, 1H), 3.88 (s, 2H), 3.77 (s, 2H), 2.93 (t, 2H), 2.62 (m, 2H). ES-LC/MS m/z=558 [M+H]+.

Workup

  1. customThe reaction mixture was evaporated down
  2. washwashed with brine
  3. customPurification via column chromatography

Sources & evidence

ORD record
ord-b13e4055ce0542bbaf43eb7b5ff1e427
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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