Dimethylformamide → HCID 10002930, compound

HRID 222734Notes

Reaction equation

HRID 222734 reaction equation
[CH:1]1([N:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[C:13]([OH:16])[CH:14]=[CH:15][C:8]=3[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.Cl[C:18]1[N:23]=[CH:22][C:21]([C:24]2[N:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([O:32][CH3:33])[N:25]=2)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Ca+2].CN(C)C=O>C(OCC)(=O)C>[CH:1]1([N:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[C:13]([O:16][C:18]4[CH:19]=[CH:20][C:21]([C:24]5[N:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([O:32][CH3:33])[N:25]=5)=[CH:22][N:23]=4)[CH:14]=[CH:15][C:8]=3[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10112Calcium CarbonateHCID 5180781HCID 5180781, compoundHCID 100820813-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[D]azepin-7-OL

Product 1

HCID 10002930HCID 10002930, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol (E3) (125 mg, 0.58 mmol), 2-(6-chloro-pyridin-3-yl)-4,6-dimethoxy-pyrimidine (145 mg, 0.58 mmol), calcium carbonate (720 mg, 2.2 mmol) and dimethylformamide (4 ml) were heated in a microwave reactor at 180° C. for 900 seconds at 300 W. The mixture was diluted with ethyl acetate, washed with water, then brine and dried over sodium sulphate. The residue was purified by column chromatography eluting with a mixture of 0.880 ammonia:methanol:dichloromethane (0.2:1.8:98) to afford the title product. MS (ES+) m/e 433 [M+H]+.

Workup

  1. washwashed with water
  2. dry with materialbrine and dried over sodium sulphate
  3. customThe residue was purified by column chromatography
  4. washeluting with a mixture of 0.880 ammonia:methanol:dichloromethane (0.2:1.8:98)

Sources & evidence

ORD record
ord-834b208068614c6992a83b6d6b0816ad
Source dataset
uspto-grants-2012_06
Patent number
US08207331B2

Reaction notes

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