Dimethylamine → HCID 46917655, compound

HRID 1619892Notes

Reaction equation

HRID 1619892 reaction equation
[F:1][CH:2]([F:40])[C:3]1[N:7]([C:8]2[N:13]=[C:12]3[N:14]([CH:17]4[CH2:22][CH2:21][N:20]([S:23]([CH:26]=[CH2:27])(=[O:25])=[O:24])[CH2:19][CH2:18]4)[N:15]=[CH:16][C:11]3=[C:10]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[N:9]=2)[C:6]2[CH:34]=[CH:35][CH:36]=[C:37]([O:38][CH3:39])[C:5]=2[N:4]=1.[CH3:41][NH:42][CH3:43]>C1COCC1.O>[F:40][CH:2]([F:1])[C:3]1[N:7]([C:8]2[N:13]=[C:12]3[N:14]([CH:17]4[CH2:18][CH2:19][N:20]([S:23]([CH2:26][CH2:27][N:42]([CH3:43])[CH3:41])(=[O:24])=[O:25])[CH2:21][CH2:22]4)[N:15]=[CH:16][C:11]3=[C:10]([N:28]3[CH2:29][CH2:30][O:31][CH2:32][CH2:33]3)[N:9]=2)[C:6]2[CH:34]=[CH:35][CH:36]=[C:37]([O:38][CH3:39])[C:5]=2[N:4]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 66698258HCID 66698258, compound

Product 1

HCID 46917655HCID 46917655, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of the above vinylsulfonamide (140 mg, 0.243 mmol) in 100 mL THF was treated with 10 mL of 40% aq. dimethylamine to give a clear solution. After 10 min, the mixture was diluted with water and the THF was removed under vacuum to give 140 mg (93% yield) of N-[2-({4-[6-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-4-(4-morpholinyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl}sulfonyl)ethyl]-N,N-dimethylamine as a white solid: 1H NMR (CDCl3) δ 7.99 (s, 1H), 7.82 (dd, J=8.4, 0.6 Hz, 1H), 7.45 (t, JHF=53.6 Hz, 1H), 7.37 (t, J=8.2 Hz, 1H), 6.83 (d, J=7.8 Hz, 1H), 4.85 (tt, J=11.1, 4.1 Hz, 1H), 4.07 (s, 3H), 4.06 (m, 4H), 4.02 (m, 1H), 3.98 (m, 1H), 3.91 (m, 4H), 3.18-3.07 (m, 4H), 2.80 (dd, J=8.3, 6.4 Hz, 2H), 2.41 (dq, J=11.7, 4.2 Hz, 2H), 2.29 (s, 6H), 2.14 (dd, J=12.5, 2.5 Hz, 2H).

Workup

  1. customto give a clear solution
  2. customthe THF was removed under vacuum

Sources & evidence

ORD record
ord-b2963e36421940138aba0f2450e86bd5
Source dataset
uspto-grants-2014_07
Patent number
US08772287B2

Reaction notes

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