Morpholine → [3-Chloro-2-fluoro-5-(morpholine-4-carbonyl)-benzyl]-carbamic acid tert-butyl ester

HRID 1527511Notes

Reaction equation

HRID 1527511 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([Cl:20])[C:18]=1[F:19])[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:45]1[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[CH:11]=[C:12]([C:13]([N:45]2[CH2:50][CH2:49][O:48][CH2:47][CH2:46]2)=[O:15])[CH:16]=[C:17]([Cl:20])[C:18]=1[F:19])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 682834143-(Tert-butoxycarbonylamino-methyl)-5-chloro-4-fluoro-benzoic acid

Product 1

HCID 68283707[3-Chloro-2-fluoro-5-(morpholine-4-carbonyl)-benzyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

was prepared according to Scheme C3 (step A) from 3-(tert-butoxycarbonylamino-methyl)-5-chloro-4-fluoro-benzoic acid (125 mg, 0.41 mmol), HATU (235 mg, 0.62 mmol), morpholine (43 mg, 0.49 mmol) and DIPEA (0.22 mL, 1.2 mmol) in DMF (2 mL). MS (LC-MS): 317.0 [M−55]+; tR (HPLC conditions c): 4.65 min.

Workup

  1. customwas prepared
  2. custom4.65 min.

Sources & evidence

ORD record
ord-7391fdac29ae44bb88d72efa7f0b6f28
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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