HCID 86762757, compound → N-[(4aR,7aS)-7a-(3-bromophenyl)-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

HRID 876727Notes

Reaction equation

HRID 876727 reaction equation
C([N:4]1[CH2:12][C@@H:11]2[C@@:6]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Br:28])[CH:23]=3)([N:7]=[C:8]([NH:13][C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[S:9][CH2:10]2)[CH2:5]1)C=C>C(Cl)(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:28][C:24]1[CH:23]=[C:22]([C@:6]23[CH2:5][NH:4][CH2:12][C@H:11]2[CH2:10][S:9][C:8]([NH:13][C:14](=[O:21])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[N:7]3)[CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 1

HCID 86762757HCID 86762757, compound

Product 1

HCID 57827645N-[(4aR,7aS)-7a-(3-bromophenyl)-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6212ChloroformSolvent

Procedure

In a separate flask, a mixture of N-[(4aR,7aS)-6-allyl-7a-(3-bromophenyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide (22.2 g, 48.6 mmol) and N,N-dimethylbarbituric acid (19.28 g, 121.6 mmol) in chloroform (486 mL) is degassed by bubbling nitrogen through the resulting slurry at RT for 5 min. The mixture is treated with tetrakis(triphenylphosphine)palladium (5.79 g, 4.86 mmol) and is stirred for 2 hours under nitrogen.

Workup

  1. customis degassed
  2. customby bubbling nitrogen through the resulting slurry at RT for 5 min

Sources & evidence

ORD record
ord-b8bb97468b364cd390df2e7199437ede
Source dataset
uspto-grants-2015_03
Patent number
US08987254B2

Reaction notes

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