2-(2,5-Dichloro-pyrimidin-4-ylamino)-N,N-dimethyl-benzenesulfonamide → HCID 66830019, compound

HRID 1041367Notes

Reaction equation

HRID 1041367 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([CH2:15][CH3:16])[C:7](=[O:14])[CH:8]([N:11]([CH3:13])[CH3:12])[CH2:9][CH2:10][C:4]=2[C:3]=1[O:19][CH3:20].Cl[C:22]1[N:27]=[C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[S:35]([N:38]([CH3:40])[CH3:39])(=[O:37])=[O:36])[C:25]([Cl:41])=[CH:24][N:23]=1>>[Cl:41][C:25]1[C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[S:35]([N:38]([CH3:40])[CH3:39])(=[O:37])=[O:36])=[N:27][C:22]([NH:1][C:2]2[CH:18]=[CH:17][C:5]3[N:6]([CH2:15][CH3:16])[C:7](=[O:14])[CH:8]([N:11]([CH3:12])[CH3:13])[CH2:9][CH2:10][C:4]=3[C:3]=2[O:19][CH3:20])=[N:23][CH:24]=1

Participants

3

Reactant 2

HCID 467382872-(2,5-Dichloro-pyrimidin-4-ylamino)-N,N-dimethyl-benzenesulfonamideHCID 67264559HCID 67264559, compound

Product 1

HCID 66830019HCID 66830019, compoundYield 15.9%

Procedure

Following a procedure analogous to Example 113, 7-Amino-3-dimethylamino-1-ethyl-6-methoxy-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (78 mgs) and 2-(2,5-Dichloro-pyrimidin-4-ylamino)-N,N-dimethyl-benzenesulfonamide (89 mgs) were converted to the title compound as a tan solid (24 mgs). 1H-NMR (CDCl3, 400 MHz): 9.49 (s, 1H), 8.38 (d, J=8.1 Hz, 1H), 8.27 (d, J=8.9 Hz, 1H), 8.20 (s, 1H), 7.92 (d, J=8.1 Hz, 1H), 7.64 (d, J=8.1 Hz, 1H), 7.49 (s, 1H), 7.31-7.28 (m, 1H), 6.94 (d, J=9.1 Hz, 1H), 4.32-4.26 (m, 1H), 3.83 (s, 3H), 3.54-3.48 (m, 2H), 3.15-3.08 (m, 1H), 3.00-2.95 (m, 1H), 2.78 (s, 6H), 2.65-2.10 (m, 8H), 1.27-1.24 (m, 2H), 1.15 (t, J=7.1 Hz, 3H). LC/MS found (M+H)+=588.21

Sources & evidence

ORD record
ord-2885d808bfca4b05a3c7e775517bc329
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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