Citric Acid → HCID 67263936, compound

HRID 1040583Notes

Reaction equation

HRID 1040583 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][N:5]1[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][C:7]2[CH:13]=[C:14]([NH:17][C:18]3[N:23]=[C:22]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[S:31](=[O:35])(=[O:34])[NH:32][CH3:33])[C:21]([Cl:36])=[CH:20][N:19]=3)[CH:15]=[CH:16][C:6]1=2.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[Cl:36][C:21]1[C:22]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[S:31](=[O:35])(=[O:34])[NH:32][CH3:33])=[N:23][C:18]([NH:17][C:14]2[CH:15]=[CH:16][C:6]3[N:5]([CH2:4][C:3]([OH:37])=[O:2])[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][C:7]=3[CH:13]=2)=[N:19][CH:20]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 66829630HCID 66829630, compound

Product 1

HCID 67263936HCID 67263936, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

{7-[5-Chloro-4-(2-methylsulfamoyl-phenylamino)-pyrimidin-2-ylamino]-2-oxo-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl}-acetic acid methyl ester (67 mg, 0.123 mmol) was taken up in THF (1 ml). 1N NaOH (1 ml) was added, and the mixture was stirred 18 hours at room temperature. 10% citric acid was added to make the mixture acidic. It was washed with ethyl acetate, and the organic phase was then washed with water, concentrated, and triturated with dichloromethane. Filtration yielded the title compound as a tan solid, 44 mg. (69% yield) 1H NMR (400 MHz, DMSO-d6) δ 12.69 (s, 1H), 9.57 (s, 1H), 9.27 (s, 1H), 8.40-8.52 (m, 1H), 8.29 (s, 1H), 7.70-7.86 (m, 2H), 7.42-7.68 (m, 3H), 7.24-7.32 (m, 1H), 7.09-7.15 (m, 1H), 4.36 (s, 2H), 2.58-2.85 (m, 2H), 2.35 (s, 3H), 1.95-2.23 (s, 4H); MS (m/e) 531 (M+1); mp 192-195° C.; retention time 6.97 minute.

Workup

  1. washIt was washed with ethyl acetate
  2. washthe organic phase was then washed with water
  3. concentrationconcentrated
  4. customtriturated with dichloromethane
  5. filtrationFiltration

Sources & evidence

ORD record
ord-500102515cda4294b91ab96c91553f67
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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