4-Morpholinecarbonyl chloride → HCID 59375076, compound

HRID 661947Notes

Reaction equation

HRID 661947 reaction equation
[N:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[C:29]2[C:28]3[C:23](=[CH:24][C:25]([OH:30])=[CH:26][CH:27]=3)[NH:22][C:21]=2[C:20]([C:31]([NH2:33])=[O:32])=[CH:19][CH:18]=1>N1C=CC=CC=1.CCOC(C)=O>[N:1]1([C:7]([O:30][C:25]2[CH:26]=[CH:27][C:28]3[C:29]4[C:21](=[C:20]([C:31](=[O:32])[NH2:33])[CH:19]=[CH:18][C:17]=4[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=4[F:10])[NH:22][C:23]=3[CH:24]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 848104-Morpholinecarbonyl chloride2×HCID 59375146HCID 59375146, compound

Product 1

HCID 59375076HCID 59375076, compoundYield 31.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Morpholine-4-carbonyl chloride (11.29 mg, 0.075 mmol) was added to a solution of 4-(2-fluorophenyl)-7-hydroxy-9H-carbazole-1-carboxamide (Example 40-1, 18.6 mg, 0.058 mmol) in pyridine (1 mL). After 22 h at rt, additional morpholine-4-carbonyl chloride (11.29 mg, 0.075 mmol) was added. After 15 h, the mixture was diluted with EtOAc (30 mL), washed with water (10 mL) and brine (5 mL), and dried and concentrated. The residue was purified by preparative HPLC to provide 8-carbamoyl-5-(2-fluorophenyl)-9H-carbazol-2-yl morpholine-4-carboxylate as a white solid (7.9 mg, 27%). 1H NMR (400 MHz, chloroform-d) δ 9.94 (1H, br. s.), 7.41-7.65 (3H, m), 7.33 (2H, t, J=8.14 Hz), 7.20 (1H, d, J=8.58 Hz), 6.92-7.15 (4H, m), 6.73 (1H, dd, J=8.58, 1.98 Hz), 3.80 (4H, t, J=4.62 Hz), 3.67-3.76 (2H, m), 3.62 (2H, br. s.). Mass spectrum m/z 434.0 (M+H)+.

Workup

  1. waitAfter 15 h
  2. washwashed with water (10 mL) and brine (5 mL)
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-4ccc04174d1b4cf78c974d6a8f41c995
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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