2-(2,5-Dichloro-pyrimidin-4-ylamino)-N,N-dimethyl-benzenesulfonamide → HCID 25159008, compound

HRID 1041204Notes

Reaction equation

HRID 1041204 reaction equation
[CH3:1][O:2][C:3]1[C:13]2[CH2:12][CH2:11][CH2:10][CH:9]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH2:8][C:7]=2[C:6]([NH2:20])=[CH:5][CH:4]=1.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:20][C:6]2[C:7]3[CH2:8][CH:9]([N:14]4[CH2:15][CH2:16][O:17][CH2:18][CH2:19]4)[CH2:10][CH2:11][CH2:12][C:13]=3[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[N:23][CH:24]=1

Participants

3

Reactant 2

HCID 467382872-(2,5-Dichloro-pyrimidin-4-ylamino)-N,N-dimethyl-benzenesulfonamideHCID 67264662HCID 67264662, compound

Product 1

HCID 25159008HCID 25159008, compound

Procedure

The title compound was prepared from 4-methoxy-8-morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-1-ylamine (50 mg, 0.2 mmol) and 2-(2,5-dichloropyrimidin-4-ylamino)-N,N-dimethylbenzenesulfonamide (70 mg, 0.2 mmol) in an analogous manner to Example 944 to afford a white foam (49 mg, 50%). Mp: 196-8° C. LCMS (m/e) 587 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 9.60 (s, 1H), 8.07 (m, 1H), 7.80 (d, J=8 Hz, 1H), 7.25 (m, 1H), 7.19 (d, J=9 Hz, 1H), 7.11 (m, 1H), 6.81 (d, J=9 Hz, 1H), 6.70 (br s, 1H), 3.86 (s, 3H), 3.60 (m, 4H), 3.42 (m, 1H), 3.22 (m, 1H), 2.75 (s, 6H), 2.59 (m, 3H), 2.33 (m, 4H), 2.00 (m, 3H), 1.72 (m, 1H).

Sources & evidence

ORD record
ord-c49f76aa2a294cf9b6d35ee0abc9d450
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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