Picolinoyl Chloride Hydrochloride → HCID 59375137, compound

HRID 661973Notes

Reaction equation

HRID 661973 reaction equation
[NH2:1][C:2]1[C:3]([CH3:35])=[C:4]([C:8]2[CH:20]=[CH:19][C:18]([C:21](=[O:23])[NH2:22])=[C:17]3[C:9]=2[C:10]2[CH2:11][CH2:12][CH:13]([NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:14][C:15]=2[NH:16]3)[CH:5]=[CH:6][CH:7]=1.Cl.[N:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[C:43](Cl)=[O:44]>C(Cl)Cl>[C:21]([C:18]1[CH:19]=[CH:20][C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:43](=[O:44])[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][N:37]=3)[C:3]=2[CH3:35])=[C:9]2[C:17]=1[NH:16][C:15]1[CH2:14][CH:13]([NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:12][CH2:11][C:10]2=1)(=[O:23])[NH2:22]

Participants

4

Reactant 2

HCID 135033Picolinoyl Chloride HydrochlorideHCID 59375069HCID 59375069, compound

Product 1

HCID 59375137HCID 59375137, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzyl 5-(3-amino-2-methylphenyl)-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazol-2-ylcarbamate, TFA salt (Example 51-1, 55 mg, 0.094 mmol), TEA (0.066 mL, 0.472 mmol), and picolinoyl chloride hydrochloric acid salt (50.4 mg, 0.283 mmol) in DCM (8 mL) was stirred at rt overnight. The mixture was concentrated and purified by preparative HPLC to provide benzyl 8-carbamoyl-5-(2-methyl-3-(picolinamido)phenyl)-2,3,4,9-tetrahydro-1H-carbazol-2-ylcarbamate, isolated as the TFA salt, as a white solid (26 mg, 39%). 1H NMR (400 MHz, methanol-d4) δ 8.59 (1H, t, J=4.8 Hz), 8.14 (1H, d, J=8.3 Hz), 7.89-7.99 (1H, m), 7.85 (1H, dd, J=9.9, 8.1 Hz), 7.50 (2H, dd, J=7.7, 2.0 Hz), 7.11-7.32 (6H, m), 7.01 (1H, d, J=7.9 Hz), 6.74 (1H, d, J=7.5 Hz), 4.96 (2H, s), 3.68-3.87 (1H, m), 2.96-3.10 (1H, m), 2.49-2.66 (1H, m), 1.82-2.11 (5H, m), 1.73 (1H, br. s.), 1.34-1.62 (1H, m). Mass spectrum m/z 575.1 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-d0f936700e8a44f78c35bb9c16c39dd8
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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