2-Pyrrolidinecarboxamide, 4-fluoro-, hydrochloride (1:1), (2S,4S)- → (2S,4S)-4-fluoro-1-(2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl)pyrrolidine-2-carboxamide

HRID 886401Notes

Reaction equation

HRID 886401 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[N:18]=[C:17]3[N:11]([CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21](O)[N:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][C:6]([CH3:24])=[N:5]1)([CH3:3])[CH3:2].[CH2:25]1[C@@H:29]([C:30]([NH2:32])=[O:31])[NH:28][CH2:27][C@H:26]1[F:33].Cl>>[F:33][C@@H:26]1[CH2:27][N:28]([C:21]2[N:20]=[CH:19][C:16]3[C:17]4[N:11]([CH:10]=[C:9]([C:8]5[N:4]([CH:1]([CH3:2])[CH3:3])[N:5]=[C:6]([CH3:24])[N:7]=5)[N:18]=4)[CH2:12][CH2:13][O:14][C:15]=3[CH:22]=2)[C@H:29]([C:30]([NH2:32])=[O:31])[CH2:25]1

Participants

3

Reactant 2

HCID 451589172-Pyrrolidinecarboxamide, 4-fluoro-, hydrochloride (1:1), (2S,4S)-HCID 178432612HCID 178432612, compound

Product 1

HCID 58205032(2S,4S)-4-fluoro-1-(2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl)pyrrolidine-2-carboxamideYield 42%

Procedure

Following the procedures of Example 339, 2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulen-8-ol and 4-cis-fluoro-L-prolinamide hydrochloride with added TEA (2.5 eq.), were reacted and the crude product recrystallised from IMS/DCM to give 382 as a white solid (68 mg, 42%). LCMS: RT=2.58 min, [M+H]+ 441. 1H NMR 400 MHz (DMSO-d6) δ: 9.04 (1H, s), 7.76 (1H, s), 7.10 (1H, s), 6.91 (1H, s), 5.95 (1H, s), 5.87-5.80 (1H, m), 5.42 (1H, s), 5.29 (1H, s), 4.49-4.36 (5H, m), 3.74-3.73 (2H, m), 2.46-2.45 (1H, m), 2.20 (3H, s), 1.40 (6H, dd, J=6.59, 3.37 Hz)

Workup

  1. customwere reacted
  2. customthe crude product recrystallised from IMS/DCM

Sources & evidence

ORD record
ord-5efba87eb82a443bb980abeffc605c25
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

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