[(2-chloroethyl)sulfanyl]acetic acid → HCID 118519612, compound

HRID 1050210Notes

Reaction equation

HRID 1050210 reaction equation
[Cl:1][CH2:2][CH2:3][S:4][CH2:5][C:6]([OH:8])=O.[NH2:9][CH2:10][C@H:11]1[C@H:19]2[N:14]([C:15]3[CH:23]=[CH:22][C:21]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][C:25]4=[O:30])=[CH:20][C:16]=3[O:17][CH2:18]2)[C:13](=[O:31])[O:12]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[Cl:1][CH2:2][CH2:3][S:4][CH2:5][C:6]([NH:9][CH2:10][C@H:11]1[C@H:19]2[N:14]([C:15]3[CH:23]=[CH:22][C:21]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][C:25]4=[O:30])=[CH:20][C:16]=3[O:17][CH2:18]2)[C:13](=[O:31])[O:12]1)=[O:8]

Participants

4

Reactant 3

HCID 230247[(2-chloroethyl)sulfanyl]acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90295505HCID 90295505, compound

Product 1

HCID 118519612HCID 118519612, compoundYield 61.3%

Procedure

Using compound 2-((2-chloroethyl)thio) acetic acid (58 mg, 0.377 mmol), compound (3S,3aS)-3-aminomethyl-7-(3-oxomorpholin-4-yl)-3a,4-dihydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-1 (3H)-one (the product of step (e) in Example 1) (80 mg, 0.251 mmol), TEA (76.2 mg, 0.753 mmol), and HATU (171 mg, 0.452 mmol) as starting materials, preparation following the method as described in Example 11 (g) afforded white solid 70 mg, yield 61.3%.

Workup

  1. custommaterials, preparation

Sources & evidence

ORD record
ord-2f5ed4ca873249018ffbbf40424b320c
Source dataset
uspto-grants-2016_07
Patent number
US09382265B2

Reaction notes

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