Isopropanol → HCID 178425838, compound

HRID 1041224Notes

Reaction equation

HRID 1041224 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[NH:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[N:19]=2)[C:5]([Cl:24])=[CH:4][N:3]=1.[NH2:25][C:26]1[CH:39]=[CH:38][C:29]2[NH:30][C:31](=[O:37])[CH2:32][CH2:33][C:34]([CH3:36])([CH3:35])[C:28]=2[CH:27]=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C(O)(C)C>>[Cl:24][C:5]1[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[NH:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[N:19]=2)=[N:7][C:2]([NH:25][C:26]2[CH:39]=[CH:38][C:29]3[NH:30][C:31](=[O:37])[CH2:32][CH2:33][C:34]([CH3:36])([CH3:35])[C:28]=3[CH:27]=2)=[N:3][CH:4]=1

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 578538307-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-oneHCID 178506249HCID 178506249, compound

Product 1

HCID 178425838HCID 178425838, compoundYield 26.5%

Procedure

(2,5-Dichloro-pyrimidin-4-yl)-[2-(4-trifluoromethyl-1H-imidazol-2-yl)-phenyl]-amine (50.0 mg, 0.134 mmol), 7-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (27.0 mg, 0.132 mmol) and 10-Camphorsulfonic acid (31.0 mg, 0.133 mmol) were suspended in Isopropyl alcohol (3.0 mL, 0.039 mol) and the reaction was microwaved on 300 watts, 140° C. for 20 minutes. The reaction mixture was then reduced under nitrogen and the crude residue was isolated and purified by prep HPLC to afford 18.95 mg (26%) of the desired product as a TFA salt. LC/MS (ESI): 558.26. 1H NMR (400 MHz, DMSO, d6) δ 9.46 (s, 1H), 9.39 (s, 1H), 8.96 (m, 1H), 8.23 (s, 1H), 8.08 (s, 1H), 7.97 (m, 1H), 7.66 (m, 1H), 7.54 (m, 1H), 7.39 (m, 1H), 7.21 (m, 1H), 6.91 (d, 1H, J=8.59 Hz), 2.16 (m, 2H), 1.98 (m, 2H), 1.29 (s, 6H).

Workup

  1. customthe reaction was microwaved on 300 watts, 140° C. for 20 minutes
  2. customthe crude residue was isolated
  3. custompurified by prep HPLC

Sources & evidence

ORD record
ord-886efe8832fb49f09264ef87369f5836
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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