Hydrochloric Acid → HCID 59121898, compound

HRID 1990927Notes

Reaction equation

HRID 1990927 reaction equation
C1(S([N:10]2[C:14]3[N:15]=[C:16]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:17]=[C:18]([NH:19][CH2:20][C@H:21]([OH:24])[CH2:22][OH:23])[C:13]=3[CH:12]=[C:11]2[C:31]([N:33]2[CH2:38][CH2:37][C:36]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[Cl:47])([C:39]#[N:40])[CH2:35][CH2:34]2)=[O:32])(=O)=O)C=CC=CC=1.[OH-].[Na+].Cl>CO>[Cl:47][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=1[C:36]1([C:39]#[N:40])[CH2:37][CH2:38][N:33]([C:31]([C:11]2[NH:10][C:14]3[N:15]=[C:16]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:17]=[C:18]([NH:19][CH2:20][C@H:21]([OH:24])[CH2:22][OH:23])[C:13]=3[CH:12]=2)=[O:32])[CH2:34][CH2:35]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68569110HCID 68569110, compound

Product 1

HCID 59121898HCID 59121898, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-1-[7-Benzene-sulfonyl-4-(2,3-dihydroxypropylamino)-2-phenyl-7H-pyrrolo[2,3-d]-pyrimidine-6-carbonyl]-4-(2-chlorophenyl)piperidine-4-carbonitrile 31.c (55 mg) was stirred in MeOH and treated with 1 M NaOH aqueous solution at rt under nitrogen for 2 h. The resulting mixture was neutralized with 3M HCl aqueous solution (pH=7). The solvent was then removed in vacuo. The residue was dissolved in DCM+MeOH and charged onto a TLC plate. A white foam (29 mg) was obtained in 67% yield. 1H-NMR (200 MHz, CDCl3+MeOH-d4): δ=1.95-2.20 (m, 2H), 2.50-2.70 (m, 2H), 3.40-3.70 (m, 4H), 3.78-3.95 (m, 3H), 4.65-4.78 (m, 2H), 6.75 (s, 1H), 7.25-7.47 (m, 7H), 8.18-8.23 (m, 4H). MS (ES): 531.0 [MH+].

Workup

  1. customThe solvent was then removed in vacuo
  2. dissolutionThe residue was dissolved in DCM+MeOH
  3. additioncharged onto a TLC plate

Sources & evidence

ORD record
ord-491b2e5a55a340fe90352e38abb4bed9
Source dataset
uspto-grants-2010_01
Patent number
US07645754B2

Reaction notes

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