2-(2,5-Dichloro-pyrimidin-4-ylamino)-N,N-dimethyl-benzenesulfonamide → HCID 66830080, compound

HRID 1041371Notes

Reaction equation

HRID 1041371 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]([CH2:18][CH3:19])[C:7](=[O:17])[CH:8]([NH:11][C:12]([CH:14]3[CH2:16][CH2:15]3)=[O:13])[CH2:9][CH2:10][C:4]=2[C:3]=1[O:22][CH3:23].Cl[C:25]1[N:30]=[C:29]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[S:38]([N:41]([CH3:43])[CH3:42])(=[O:40])=[O:39])[C:28]([Cl:44])=[CH:27][N:26]=1>>[Cl:44][C:28]1[C:29]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[S:38](=[O:40])(=[O:39])[N:41]([CH3:42])[CH3:43])=[N:30][C:25]([NH:1][C:2]2[CH:21]=[CH:20][C:5]3[N:6]([CH2:18][CH3:19])[C:7](=[O:17])[CH:8]([NH:11][C:12]([CH:14]4[CH2:15][CH2:16]4)=[O:13])[CH2:9][CH2:10][C:4]=3[C:3]=2[O:22][CH3:23])=[N:26][CH:27]=1

Participants

3

Reactant 2

HCID 467382872-(2,5-Dichloro-pyrimidin-4-ylamino)-N,N-dimethyl-benzenesulfonamideHCID 67264091HCID 67264091, compound

Product 1

HCID 66830080HCID 66830080, compound

Procedure

Following a procedure analogous to Example 113 Cyclopropanecarboxylic acid (7-amino-1-ethyl-6-methoxy-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)-amide (45 mgs) and 2-(2,5-Dichloro-pyrimidin-4-ylamino)-N,N-dimethyl-benzenesulfonamide was converted to the title compound (48 mgs). 1H NMR (400 MHz, (CD3)2SO) δ 9.41 (s, 1H), 8.70 (s, 1H), 8.55 (d, J=8.1 Hz, 1H), 8.39 (d, J=8.8 Hz, 1H), 8.28 (s, 1H), 7.78 (d, J=7.8 Hz, 1H), 7.67 (d, J=9.1 Hz, 1H), 7.57 (t, J=7.8 Hz, 1H), 7.27 (t, J=7.7 Hz, 1H), 7.14 (d, J=8.6 Hz, 1H), 4.19-4.30 (m, 2H), 3.69 (s, 3H), 3.48 (m, 1H), 3.04 (dd, J=13.7 Hz, J=5.4 Hz, 1H), 2.65 (s, 6H), 2.33-2.41 (m, 1H), 2.04-2.12 (m, 2H), 1.67 (m, 1H), 1.02 (t, J=6.8 Hz, 3H), 0.56-0.67 (m, 4H). LCMS: found 629.11 (m+1).

Sources & evidence

ORD record
ord-d67343bfa0914ef6a60a59065f4fa07d
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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