Isopropanol → HCID 66830633, compound

HRID 1687534Notes

Reaction equation

HRID 1687534 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=2[C:11]([NH:13][CH2:14][CH2:15][CH3:16])=[O:12])[C:5]([Cl:21])=[CH:4][N:3]=1.[NH2:22][C:23]1[CH:36]=[CH:35][C:26]2[NH:27][C:28](=[O:34])[CH2:29][CH2:30][C:31]([CH3:33])([CH3:32])[C:25]=2[CH:24]=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C(O)(C)C>>[Cl:21][C:5]1[C:6]([NH:8][C:9]2[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=2[C:11]([NH:13][CH2:14][CH2:15][CH3:16])=[O:12])=[N:7][C:2]([NH:22][C:23]2[CH:36]=[CH:35][C:26]3[NH:27][C:28](=[O:34])[CH2:29][CH2:30][C:31]([CH3:33])([CH3:32])[C:25]=3[CH:24]=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 86633964HCID 86633964, compound

Product 1

HCID 66830633HCID 66830633, compoundYield 38%

Procedure

2-(2,5-Dichloro-pyrimidin-4-ylamino)-N-propyl-benzamide (50.0 mg, 0.000154 mol), 7-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (31.4 mg, 0.000154 mol) and 10-Camphorsulfonic acid (35.7 mg, 0.000154 mol) were dissolved in Isopropyl alcohol (3.00 mL, 0.0392 mol) and the reaction was microwaved on 300 watts, 140° C. for 20 minutes. The reaction mixture was reduced under nitrogen. The crude residue was isolated and purified by prep HPLC to afford 28.57 mg (38%) of the title compound. LC/MS (ESI): 493.17. 1H NMR (400 MHz, DMSO, d6) δ 9.44 (s, 1H), 9.37 (s, 1H), 8.76 (m, 2H), 8.21 (s, 1H), 7.76 (d, 1H, J=7.83 Hz), 7.65 (d, 1H, J=8.08 Hz), 7.48 (m, 2H), 7.14 (t, 1H, J=7.33 Hz), 6.88 (d, 1H, J=8.34 Hz), 3.25 (m, 2H), 2.17 (m, 2H), 1.97 (m, 2H), 1.55 (m, 2H), 1.29 (s, 6H), 0.90 (t, 3H, J=7.33 Hz).

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-2191fa064ec146b68b46f2137cfe232b
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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