Diisopropylethylamine → HCID 71611282, compound

HRID 2409069Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[CH:5]=[CH:4][N:3]=1.[NH2:17][CH:18]([C:20]1[CH:21]=[C:22]2[CH:28]=[CH:27][N:26](C(OC(C)(C)C)=O)[C:23]2=[CH:24][N:25]=1)[CH3:19].CCN(C(C)C)C(C)C>CCCCO>[NH:26]1[C:23]2=[CH:24][N:25]=[C:20]([CH:18]([NH:17][C:2]3[N:7]=[C:6]([NH:8][C:9]4[CH:13]=[C:12]([CH:14]5[CH2:16][CH2:15]5)[NH:11][N:10]=4)[CH:5]=[CH:4][N:3]=3)[CH3:19])[CH:21]=[C:22]2[CH:28]=[CH:27]1

Participants

Conditions

Temperature: 115 °C

Procedure

A sealed-cap vial was charged with 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-pyrimidin-4-amine (60 mg, 0.25 mmol), tert-butyl 5-(1-aminoethyl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate (93 mg, 0.36 mmol), DIPEA (0.16 mL) and n-BuOH (0.8 mL). The mixture was heated at 115° C. for 72 h. The reaction mixture was concentrated under reduced pressure. The crude mixture was purified by preparative HPLC to afford N2-(1-(1H-pyrrolo[2,3-c]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine: MS (ESI) m/z: 361.2 [M+1]+.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customThe crude mixture was purified by preparative HPLC

Sources & evidence

ORD record: ord-58a6d785bd024b5ebca189da57c74124
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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