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N,N-Dimethylglycine → HCID 68501766, compound

HRID 1714022
Notes
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Reaction equation

HRID 1714022 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:27]([O:29][CH3:30])=[O:28])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][NH:19][CH2:18][C:17]4[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[CH3:40][N:41]([CH3:46])[CH2:42][C:43](O)=[O:44].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.Cl>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:27]([O:29][CH3:30])=[O:28])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][N:19]([C:43](=[O:44])[CH2:42][N:41]([CH3:46])[CH3:40])[CH2:18][C:17]4[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:16]=4[C:15]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68507183HCID 68507183, compound

Product 1

HCID 68501766HCID 68501766, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 14-cyclohexyl-3-fluoro-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate (from Step 5) in DCM (0.15 M), DIPEA (4 eq.), dimethylglycine (3 eq.) and HATU (2 eq.) were added and the mixture stirred at RT overnight. The solution was diluted with DCM and HCl (1N) and the 2 phases separated. The aqueous phase was extracted with DCM (twice). The combined organic phases were then washed with a saturated aqueous solution of NaHCO3 and brine before being dried (Na2SO4), filtered and concentrated in vacuo. The crude was used in the next step without further purification; MS (ES+) m/z 492 (M+H)+.

Workup

  1. customthe 2 phases separated
  2. extractionThe aqueous phase was extracted with DCM (twice)
  3. washThe combined organic phases were then washed with a saturated aqueous solution of NaHCO3 and brine
  4. dry with materialbefore being dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude was used in the next step without further purification

Sources & evidence

ORD record
ord-8f2bdac398294fe5969c1edb41002629
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07795247B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes