Triethylamine → N-(3-(isopropylcarbamoyl)phenyl)-4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

HRID 216035Notes

Reaction equation

[CH3:1][C:2]1([C:18](O)=[O:19])[CH2:7][CH2:6][N:5]([C:8]2[C:9]3[C:16]([CH3:17])=[CH:15][NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH2:4][CH2:3]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH2:52][C:53]1[CH:54]=[C:55]([CH:62]=[CH:63][CH:64]=1)[C:56]([NH:58][CH:59]([CH3:61])[CH3:60])=[O:57]>CN(C=O)C>[CH:59]([NH:58][C:56]([C:55]1[CH:54]=[C:53]([NH:52][C:18]([C:2]2([CH3:1])[CH2:3][CH2:4][N:5]([C:8]3[C:9]4[C:16]([CH3:17])=[CH:15][NH:14][C:10]=4[N:11]=[CH:12][N:13]=3)[CH2:6][CH2:7]2)=[O:19])[CH:64]=[CH:63][CH:62]=1)=[O:57])([CH3:61])[CH3:60]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4yl)-piperidine-4-carboxylic acid from example 6, step B, (0.030 g, 0.11 mmol) in DMF (1 mL) were added HATU (0.042 g, 0.11 mmol), triethylamine (0.028 mL, 0.22 mmol) and 3-amino-N-isopropyl-benzamide (0.029 mg, 0.17 mmol). The reaction was stirred at 50° C. for 48 hours and concentrated under vacuum. The residue was purified by prep HPLC to give the title compound (0.023 g, 48%).

Workup

concentrationconcentrated under vacuum
customThe residue was purified by prep HPLC

Sources & evidence

ORD record: ord-117ced0733d14ae293bdf0ce692966a2
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193202B2

Reaction notes

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