Pyrrolidine → HCID 66604547, compound

HRID 2410929Notes

Reaction equation

HRID 2410929 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([F:28])[CH:21]=2)[CH:7]=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[C:12]([C:17]([O-])=[O:18])[CH:11]=[CH:10][C:9]2=1)(=[O:3])[NH2:2].CN(C(ON1N=NC2[CH:40]=[CH:41][CH:42]=[N:43][C:38]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.N1CCCC1>CN(C=O)C>[F:28][C:22]1[CH:21]=[C:20]([C:6]2[CH:5]=[C:4]([C:1]([NH2:2])=[O:3])[C:16]3[NH:15][C:14]4[C:9]([C:8]=3[CH:7]=2)=[CH:10][CH:11]=[C:12]([C:17]([N:43]2[CH2:42][CH2:41][CH2:40][CH2:38]2)=[O:18])[CH:13]=4)[CH:25]=[CH:24][C:23]=1[O:26][CH3:27]

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86663070HCID 86663070, compound

Product 1

HCID 66604547HCID 66604547, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Carbamoyl-6-(3-fluoro-4-methoxyphenyl)-9H-carbazole-2-carboxylic acid (16 mg, 0.042 mmol, Example 395), HATU (24.12 mg, 0.063 mmol) and DIPEA (0.022 mL, 0.127 mmol) were dissolved in DMF (1 mL) and stirred for 10 minutes. Pyrrolidine (9.2 mg, 0.13 mmol) was added and the mixture shaken over night. Purification by prep HPLC gave 9.4 mg 3-(3-fluoro-4-methoxyphenyl)-7-(pyrrolidine-1-carbonyl)-9H-carbazole-1-carboxamide. HPLC retention time 4.36 min. (Ascentis 4.6×50 mm 5 um C18, 2 ml/min, 0 to 100% B in 8 minutes, then 100% B for 1 minute. Solvent A: 5% CH3CN—95% H2O—10 mM NH4OAc; Solvent B: 95% CH3CN—5% H2O—10 mM NH4OAc). MS (ESI) m/e+=432 [M+H]+.

Workup

  1. stirringthe mixture shaken over night
  2. customPurification by prep HPLC

Sources & evidence

ORD record
ord-861b61904855400dbe78fa4b3e15d76d
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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