Diisopropylethylamine → HCID 57920196, compound

HRID 216084Notes

Reaction equation

[CH3:1][N:2]([CH3:29])[C:3](=[O:28])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[O:13])[CH:6]=1.C(N(CC)C(C)C)(C)C.Cl[C:40]1[C:41]2[C:48]([CH3:49])=[CH:47][NH:46][C:42]=2[N:43]=[CH:44][N:45]=1>C(O)(C)C>[CH3:1][N:2]([CH3:29])[C:3](=[O:28])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([O:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:19][CH2:18][N:17]([C:40]3[C:41]4[C:48]([CH3:49])=[CH:47][NH:46][C:42]=4[N:43]=[CH:44][N:45]=3)[CH2:16][CH2:15]2)=[O:13])[CH:6]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 3-(4-(benzyloxy)piperidine-4-carboxamido)phenyl dimethylcarbamate, from step E, and N,N-diisopropylethylamine (0.7 mL, 4.02 mmol) in isopropanol (1.6 mL) was added 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (135 mg, 0.804 mmol). The reaction mixture was heated to 110° C. in a sealed high-pressure vial for 17 hours, during which time the mixture became homogenous. The reaction was concentrated under vacuum, and half of the material was purified by prep HPLC (30×100 mm C18 column, 20-100% acetonitrile:water (10 mM ammonium acetate), 15 min, 45 mL/min) to afford the title compound (33.4 mg) as a white solid.

Workup

concentrationThe reaction was concentrated under vacuum, and half of the material
customwas purified by prep HPLC (30×100 mm C18 column, 20-100% acetonitrile:water (10 mM ammonium acetate), 15 min, 45 mL/min)

Sources & evidence

ORD record: ord-84f3f823f3ab414999c40a6aef34fea6
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193202B2

Reaction notes

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