Glycine methyl ester hydrochloride → HCID 67982976, compound

HRID 1748213Notes

Reaction equation

HRID 1748213 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][C:16]([F:19])([F:18])[F:17])[C:5]=2[CH2:20][O:21][CH:22]2[CH2:28][CH:27]3[N:29]([C:30]4[S:31][C:32]5[CH:38]=[C:37]([C:39]([OH:41])=O)[CH:36]=[CH:35][C:33]=5[N:34]=4)[CH:24]([CH2:25][CH2:26]3)[CH2:23]2)[CH2:3][CH2:2]1.Cl.[CH3:43][O:44][C:45](=[O:48])[CH2:46][NH2:47].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(C(C(C)C)(CC)C([O-])=O)(C)C>ClCCl>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][C:16]([F:19])([F:17])[F:18])[C:5]=2[CH2:20][O:21][CH:22]2[CH2:23][CH:24]3[N:29]([C:30]4[S:31][C:32]5[CH:38]=[C:37]([C:39]([NH:47][CH2:46][C:45]([O:44][CH3:43])=[O:48])=[O:41])[CH:36]=[CH:35][C:33]=5[N:34]=4)[CH:27]([CH2:26][CH2:25]3)[CH2:28]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 122755Glycine methyl ester hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59053604HCID 59053604, compoundHCID 86704413HCID 86704413, compound

Product 1

HCID 67982976HCID 67982976, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)benzo[d]thiazole-6-carboxylic acid (34 mg, 0.06 mmol) was combined with glycine methyl ester hydrochloride (8 mg, 0.06 mmol), O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (25 mg, 0.065 mmol), diisopropylethylacetate (0.05 ml) and dichloromethane (2 mL). The mixture was stirred for 1 hour, then the solvent was removed in vacuo. The residue was suspended in ethyl acetate (15 mL) and washed with sodium bicarbonate solution (5 mL). The organics were combined and dried (MgSO4) then evaporated in vacuo. The product was purified by flash silica chromatography with 0-100% ethyl acetate in hexanes and used directly in the next procedure.

Workup

  1. customthe solvent was removed in vacuo
  2. washwashed with sodium bicarbonate solution (5 mL)
  3. dry with materialdried (MgSO4)
  4. customthen evaporated in vacuo
  5. customThe product was purified by flash silica chromatography with 0-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-10c9219bd0ca46e3bcc13698faea4334
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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