Ammonia → HCID 46917500, compound

HRID 516398Notes

Reaction equation

HRID 516398 reaction equation
[F:1][CH:2]([F:48])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][N:17]([S:20]([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])(=[O:22])=[O:21])[CH2:16][CH2:15]3)[N:11]=[C:10]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[N:9]=2)[C:6]2[CH:34]=[C:35]([NH:40]C(=O)OC(C)(C)C)[CH:36]=[C:37]([O:38][CH3:39])[C:5]=2[N:4]=1.N>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:40][C:35]1[CH:36]=[C:37]([O:38][CH3:39])[C:5]2[N:4]=[C:3]([CH:2]([F:48])[F:1])[N:7]([C:8]3[N:9]=[C:10]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)[N:11]=[C:12]([N:14]4[CH2:19][CH2:18][N:17]([S:20]([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])(=[O:22])=[O:21])[CH2:16][CH2:15]4)[N:13]=3)[C:6]=2[CH:34]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 66698183tert-butyl 2-(difluoromethyl)-1-[4-(4-{[2-(dimethylamino)ethyl]sulfonyl}-1-piperazinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-4-methoxy-1H-benzimidazol-6-ylcarbamate

Product 1

HCID 46917500HCID 46917500, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the above carbamate (0.244 g, 0.035 mmol) in a mixture of 10 mL CH2Cl2 and 5 mL TFA was stirred at room temperature for 2 hrs. The mixture was diluted with CH2Cl2 and then made basic with dil. aq. NH3. The organic layer was dried and concentrated to give a quantitative yield of N-[2-({4-[4-[6-amino-2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-1-piperazinyl}sulfonyl)ethyl]-N,N-dimethylamine: 1H NMR (CDCl3) δ 7.35 (t, JHF=53.8 Hz, 1H), 7.15 (d, J=1.9 Hz, 1H), 6.22 (d, J=1.9 Hz, 1H), 3.98 (m, 7H), 3.90-3.75 (m, 10H), 3.38 (m, 4H), 3.11 (dd, J=8.1, 6.5 Hz, 2H), 2.78 (dd, J=8.1, 6.4 Hz, 2H), 2.26 (s, 6H).

Workup

  1. customThe organic layer was dried
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d5ebd580202c4c39a1f2c9525f909917
Source dataset
uspto-grants-2015_08
Patent number
US09108980B2

Reaction notes

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