Diisopropylethylamine → HCID 42633351, compound

HRID 409444Notes

Reaction equation

[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]([C@H:20]1[CH2:24][C@@H:23]([CH2:25][CH3:26])[NH:22][CH2:21]1)[C:8]1[N:13]=[CH:12][C:11]([C:14]2[CH:15]=[N:16][N:17]([CH3:19])[CH:18]=2)=[CH:10][N:9]=1.Cl[C:37]1[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][N:38]=1.C(N(C(C)C)C(C)C)C>C1COCC1>[F:35][C:2]([F:34])([F:1])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]([C@H:20]1[CH2:24][C@@H:23]([CH2:25][CH3:26])[N:22]([C:37]2[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][N:38]=2)[CH2:21]1)[C:8]1[N:9]=[CH:10][C:11]([C:14]2[CH:15]=[N:16][N:17]([CH3:19])[CH:18]=2)=[CH:12][N:13]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of [3,5-bis(trifluoromethyl)benzyl]-((3S,5R)-5-ethyl-pyrrolidin-3-yl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]amine (45 mg, 0.09 mmol), 2-chloro-5-trifluoromethyl-pyridine (50 mg, 0.27 mmol) and iPr2EtN (45 uL 0.27 mmol) in THF (1.5 mL) is stirred at 120° C. under microwave irradiation. The mixture is concentrated under reduced pressure. The obtained residue is purified by silica gel column chromatography (eluent: hexane/EtOAc) to give (3,5-Bis-trifluoromethyl-benzyl)-[(3S,5R)-5-ethyl-1-(5-trifluoromethyl-pyridin-2-yl)-pyrrolidin-3-yl]-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amine as a colorless oil (38 mg, 66%). ESI-MS m/z: 643 [M+1]+, Retention time 2.45 min (condition A).

Workup

concentrationThe mixture is concentrated under reduced pressure
customThe obtained residue is purified by silica gel column chromatography (eluent: hexane/EtOAc)

Sources & evidence

ORD record: ord-f86e23adc5734d76b67fe6505c2ac8fd
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759365B2

Reaction notes

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