3,3-Difluoropyrrolidine → HCID 58529491, compound

HRID 1972841Notes

Reaction equation

HRID 1972841 reaction equation
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH:27]4[CH2:31][CH2:30][N:29]([C:32](=[O:35])[CH2:33]Cl)[CH2:28]4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:36][C:37]1([F:42])[CH2:41][CH2:40][NH:39][CH2:38]1>>[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH:27]4[CH2:31][CH2:30][N:29]([C:32](=[O:35])[CH2:33][N:39]5[CH2:40][CH2:41][C:37]([F:42])([F:36])[CH2:38]5)[CH2:28]4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27828273,3-DifluoropyrrolidineHCID 58529917HCID 58529917, compound

Product 1

HCID 58529491HCID 58529491, compoundYield 87.2%

Procedure

5-(2-benzyl-2H-indazol-6-yl)-7-[1-(chloroacetyl)pyrrolidin-3-yl]pyrrolo[2,1-f][1,2,4]triazin-4-amine (100 mg, 0.206 mmol) was reacted with 3,3-difluoropyrrolidine (44 mg, 0.412 mmol) using the procedure of Example 132 to yield 100 mg (87%) of title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.53 (s, 1 H), 7.91 (s, 1 H), 7.80 (d 1 H), 7.67 (m, 3 H), 7.38 (m, 4 H), 7.11 (d, 1 H), 6.63 (d, 1H), 5.63 (s, 2 H), 3.95-3.10 (m, 11 H), 3.05-2.60 (m, 4 H), 2.50-2.05 (m, 2 H); ES-MS m/z 557.3 [M+H]+, HPLC RT (min) 2.56.

Sources & evidence

ORD record
ord-a333d7f2f9cf48c4976b544683978914
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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