HCID 67264346, compound → HCID 67264717, compound

HRID 1041798Notes

Reaction equation

HRID 1041798 reaction equation
C(OC([N:11]1[CH2:17][C:16]2[CH:18]=[CH:19][C:20]([NH:22][C:23]3[N:28]=[C:27]([NH:29][C:30]4[C:35]([C:36](=[O:39])[NH:37][CH3:38])=[CH:34][CH:33]=[CH:32][C:31]=4[F:40])[C:26]([Cl:41])=[CH:25][N:24]=3)=[CH:21][C:15]=2[NH:14][C:13](=[O:42])[CH2:12]1)=O)C1C=CC=CC=1>CSC.FC(F)(F)C(O)=O>[Cl:41][C:26]1[C:27]([NH:29][C:30]2[C:31]([F:40])=[CH:32][CH:33]=[CH:34][C:35]=2[C:36]([NH:37][CH3:38])=[O:39])=[N:28][C:23]([NH:22][C:20]2[CH:19]=[CH:18][C:16]3[CH2:17][NH:11][CH2:12][C:13](=[O:42])[NH:14][C:15]=3[CH:21]=2)=[N:24][CH:25]=1

Participants

4

Reactant 1

HCID 67264346HCID 67264346, compound

Product 1

HCID 67264717HCID 67264717, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 1068Dimethyl SulfideSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 8-[5-chloro-4-(2-fluoro-6-methylcarbamoyl-phenylamino)-pyrimidin-2-ylamino]-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid benzyl ester (0.21 g, 0.36 mmol) in methyl sulfide (3.5 mL) and trifluoroacetic acid (11 mL) was stirred at room temperature for 16 hours. Concentration and chromatography on a silica gel with methylene chloride and methanol (20:1) gave 0.11 g of 2-[5-chloro-2-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-ylamino)-pyrimidin-4-ylamino]-3-fluoro-N-methyl-benzamide (68% yield): 1H NMR (300 MHz, CD3OD) δ 8.18 (s, 1H), 7.45 (m, 4H), 7.27 (s, 2H), 4.24 (s, 2H), 3.65 (s, 2H), 2.84 (d, 3H); MS (m/e): 456.4 (M+1).

Workup

  1. concentrationConcentration and chromatography on a silica gel with methylene chloride and methanol (20:1)

Sources & evidence

ORD record
ord-f12c1d9830c746a69f410ecdf1e4468b
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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