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N,N-Dimethylglycine → 1h-Indole-1-carboxylic acid,5-[[2-(dimethylamino)acetyl]amino]-2,3-dihydro-,1,1-dimethylethyl ester

HRID 1241894
Notes
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Reaction equation

HRID 1241894 reaction equation
FC(F)(F)[C:3]([OH:5])=[O:4].[CH2:8]([N:10]([CH3:45])[CH2:11][C:12]([N:14](C)[C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25]C3C(C(F)(F)F)=NN(C4C=C(C=CC=4)C(N)=O)C=3C2=O)=[CH:17][CH:16]=1)=[O:13])C.[CH3:46]N(C)CC(O)=O.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2[CH2:92][CH2:91][CH2:90]C2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>CCOC(C)=O.CN(C=O)C>[CH3:45][N:10]([CH3:8])[CH2:11][C:12]([NH:14][C:15]1[CH:16]=[C:17]2[C:18](=[CH:19][CH:20]=1)[N:21]([C:3]([O:5][C:91]([CH3:90])([CH3:92])[CH3:46])=[O:4])[CH2:26][CH2:25]2)=[O:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 8471TriethylamineHCID 2724699PyBOPHCID 86590502HCID 86590502, compound

Product 1

HCID 219368411h-Indole-1-carboxylic acid,5-[[2-(dimethylamino)acetyl]amino]-2,3-dihydro-,1,1-dimethylethyl esterYield 111.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

Part A. To the product (1.0 g, 4.2 mmol) from Example 2, Part B, was added N,N-dimethylglycine (490 mg, 4.7 mmol), triethylamine (1.80 ml, 13 mmol), and DMF (30 mL). To this mixture was added benzotriazol-1-yloxytripyrrolidino-phosphonium hexafluorophosphate (2.2 g, 4.3 mmol). After 10 min, the clear yellow solution was poured into EtOAc (80 mL) and washed with H2O (2×50 mL). The organic layer was washed with brine, dried over Na2SO4, and filtered. The resulting residue was purified by radial chromatography (5% MeOH in CH2Cl2) to afford tert-butyl 5-[(N,N-dimethylglycyl)amino]-1-indolinecarboxylate (1.50 g, 110%) containing a small amount of DMF. LC/MS (ESI+): 320.1 (M+H)+.

Workup

  1. washwashed with H2O (2×50 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe resulting residue was purified by radial chromatography (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-ce401932d5984819884c634c06dbcbf1
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07115627B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes