Triethylamine → tert-butyl ((4aR,11bR)-10-(5-(cyclopropylmethoxy)-3-methylpyrazine-2-carboxamido)-3,3,11b-trimethyl-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate

HRID 627758Notes

Reaction equation

HRID 627758 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:27][CH2:26][CH2:25][C@H:8]3[S:9](=[O:24])(=[O:23])[C:10]([CH3:22])([CH3:21])[C:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[N:12][C@:7]3([CH3:28])[C:6]=2[CH:29]=1.[CH:30]1([CH2:33][O:34][C:35]2[N:36]=[C:37]([CH3:44])[C:38]([C:41](O)=[O:42])=[N:39][CH:40]=2)[CH2:32][CH2:31]1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.O.C([O-])(O)=O.[Na+]>[CH:30]1([CH2:33][O:34][C:35]2[N:36]=[C:37]([CH3:44])[C:38]([C:41]([NH:1][C:2]3[CH:3]=[CH:4][C:5]4[O:27][CH2:26][CH2:25][C@H:8]5[S:9](=[O:23])(=[O:24])[C:10]([CH3:22])([CH3:21])[C:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[N:12][C@:7]5([CH3:28])[C:6]=4[CH:29]=3)=[O:42])=[N:39][CH:40]=2)[CH2:31][CH2:32]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 903014185-(Cyclopropylmethoxy)-3-methylpyrazine-2-carboxylic acidHCID 90307362tert-butyl ((4aR,11bR)-10-amino-3,3,11b-trimethyl-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate

Product 1

HCID 131735340tert-butyl ((4aR,11bR)-10-(5-(cyclopropylmethoxy)-3-methylpyrazine-2-carboxamido)-3,3,11b-trimethyl-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of crude tert-butyl ((4aR,11bR)-10-amino-3,3,11b-trimethyl-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (0.035 g, 0.083 mmol) in DCM (0.8 ml) were added 5-(cyclopropylmethoxy)-3-methylpyrazine-2-carboxylic acid (0.018 g, 0.087 mmol), triethylamine (0.023 ml, 0.165 mmol) and HATU (0.035 g, 0.091 mmol). The mixture was stirred at RT for 25 min. The reaction mixture was diluted with water and sat. NaHCO3, and extracted with DCM. The organic extract was washed with brine and dried over MgSO4. It was filtered and concentrated to give the crude material as a yellow oil which was used for next step directly. MS m/z: 614.1 [M+H].

Workup

  1. extractionextracted with DCM
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationIt was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c290b24813614e8ca4131dbfd1a48887
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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