Diisopropylethylamine → HCID 57750288, compound

HRID 423064Notes

Reaction equation

CCN(C(C)C)C(C)C.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C@H:17]([NH:19][C:20]([C:22]2([C:28]#[N:29])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[O:21])[CH3:18])=[CH:13][CH:12]=1.[CH:30]1[C:34]2[C:35](Cl)=[N:36][CH:37]=[N:38][C:33]=2[NH:32][CH:31]=1>CC(N(C)C)=O>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([C@H:17]([NH:19][C:20]([C:22]2([C:28]#[N:29])[CH2:23][CH2:24][N:25]([C:35]3[C:34]4[CH:30]=[CH:31][NH:32][C:33]=4[N:38]=[CH:37][N:36]=3)[CH2:26][CH2:27]2)=[O:21])[CH3:18])=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 90 °C

Procedure

DIPEA (1.101 mL, 6.17 mmol) was added to (R)—N-(1-(4-chlorophenyl)ethyl)-4-cyanopiperidine-4-carboxamide (Intermediate 44) (720 mg, 2.47 mmol) and 6-chloro-7-deazapurine (379 mg, 2.47 mmol) in DMA (50 mL) at 25° C. The resulting solution was stirred at 90° C. for 3 hours. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7N ammonia/MeOH and pure fractions were evaporated to dryness to afford (R)—N-(1-(4-chlorophenyl)ethyl)-4-cyano-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide (46.2%) as an orange solid. This was used in the next step without further purification.

Workup

customThe crude product was purified by ion exchange chromatography
washThe desired product was eluted from the column
customwere evaporated to dryness

Sources & evidence

ORD record: ord-49ab035fd77f4f2d914deb635542c01c
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101623B2

Reaction notes

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