Diisopropylethylamine → N2-(1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

HRID 2409071Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[N:13]([S:14]([C:17]3[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:12]=[CH:11][C:5]2=[N:6][C:7]=1[CH:8]([NH2:10])[CH3:9].CCN(C(C)C)C(C)C.Cl[C:34]1[N:39]=[C:38]([NH:40][C:41]2[CH:45]=[C:44]([CH:46]3[CH2:48][CH2:47]3)[NH:43][N:42]=2)[CH:37]=[CH:36][N:35]=1>CC(C(O)C(C)C)C>[Cl:1][C:2]1[CH:3]=[C:4]2[N:13]([S:14]([C:17]3[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:12]=[CH:11][C:5]2=[N:6][C:7]=1[CH:8]([NH:10][C:34]1[N:39]=[C:38]([NH:40][C:41]2[CH:45]=[C:44]([CH:46]3[CH2:48][CH2:47]3)[NH:43][N:42]=2)[CH:37]=[CH:36][N:35]=1)[CH3:9]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine (180 mg, 0.51 mmol), DIPEA (133 mg, 1.03 mmol), and 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (97 mg, 0.41 mmol) in 2,4-dimethyl-3-pentanol (0.5 mL) was heated at 140° C. for 18 h. The reaction mixture was concentrated under reduced pressure to afford a crude 320 mg (41%) of N2-(1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine as brown solid, which was used in the next step without further purification. MS (ESI): m/z=549.2 [M+1]+.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-80085f616b154077b226175715393be9
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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