Dimethylacetamide → HCID 58204926, compound

HRID 1800228Notes

Reaction equation

HRID 1800228 reaction equation
FC(F)(F)S(O[C:7]1[N:28]=[CH:27][C:10]2[C:11]3[N:12]([CH:16]=[C:17]([C:19]4[N:23]([CH:24]([CH3:26])[CH3:25])[N:22]=[CH:21][N:20]=4)[N:18]=3)[CH2:13][CH2:14][O:15][C:9]=2[CH:8]=1)(=O)=O.[NH:31]1[CH2:35][CH:34]=[CH:33][C@@H:32]1[C:36]([NH2:38])=[O:37].C(N(CC)C(C)C)(C)C.CN(C)C(=O)C>>[CH:24]([N:23]1[C:19]([C:17]2[N:18]=[C:11]3[C:10]4[CH:27]=[N:28][C:7]([N:31]5[CH2:35][CH:34]=[CH:33][C@@H:32]5[C:36]([NH2:38])=[O:37])=[CH:8][C:9]=4[O:15][CH2:14][CH2:13][N:12]3[CH:16]=2)=[N:20][CH:21]=[N:22]1)([CH3:25])[CH3:26]

Participants

5

Reactant 4

HCID 31374DimethylacetamideHCID 81531DiisopropylethylamineHCID 582049872-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl trifluoromethanesulfonateHCID 67050706HCID 67050706, compound

Product 1

HCID 58204926HCID 58204926, compound

Conditions

Temperature
80 °C

Procedure

A mixture of 134 mg (0.30 mmol) of 2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9-yl trifluoromethanesulfonate, (R)-2,5-dihydro-1H-pyrrole-2-carboxamide (84.1 mg, 0.750 mmol) and N,N-diisopropylethylamine (61.0 uL, 0.350 mmol) in N,N-Dimethylacetamide (3.0 mL, 32 mmol) was heated for 18 hours at 80° C. The mixture was concentrated in high vacuum, the residue triturated with 5% aqueous citric acid. The precipitate was filtered out, washed with aq. citric acid, water, dried in vacuum and purified by RP HPLC (acetonitrile gradient) to give 388. Yield 28 mg. M/z 407.2, calc. 406.19. 1H NMR (400 MHz, DMSO) δ 9.08 (s, 1H), 7.88 (s, 1H), 7.84 (s, 1H), 7.38 (s, 1H), 6.98 (s, 1H), 6.13 (dd, J=6.2, 1.9, 1H), 6.02-5.88 (m, 3H), 4.97 (s, 1H), 4.52 (dd, J=9.3, 7.1, 4H), 4.39-4.18 (m, 2H), 1.48 (dd, J=6.6, 2.5, 6H)

Workup

  1. concentrationThe mixture was concentrated in high vacuum
  2. customthe residue triturated with 5% aqueous citric acid
  3. filtrationThe precipitate was filtered out
  4. washwashed with aq. citric acid, water
  5. customdried in vacuum
  6. custompurified by RP HPLC (acetonitrile gradient)

Sources & evidence

ORD record
ord-590885c098bc4857bf2304aac4fa787b
Source dataset
uspto-grants-2013_01
Patent number
US08343955B2

Reaction notes

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