Diisopropylethylamine → HCID 68283973, compound

HRID 1527561Notes

Reaction equation

HRID 1527561 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:10]([F:25])=[C:11]([CH:22]=[CH:23][CH:24]=1)[CH2:12][NH:13][C:14]([C@@H:16]1[CH2:21][C@@H:20]2[C@@H:18]([CH2:19]2)[NH:17]1)=[O:15].[C:26]([C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]([CH2:38][C:39](O)=[O:40])[CH:30]=1)(=[O:28])[NH2:27].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:8][C:9]1[C:10]([F:25])=[C:11]([CH:22]=[CH:23][CH:24]=1)[CH2:12][NH:13][C:14]([C@@H:16]1[CH2:21][C@@H:20]2[C@@H:18]([CH2:19]2)[N:17]1[C:39](=[O:40])[CH2:38][N:31]1[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:29]([C:26]([NH2:27])=[O:28])=[CH:30]1)=[O:15]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 18071346HCID 18071346, compoundHCID 68283680HCID 68283680, compound

Product 1

HCID 68283973HCID 68283973, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The mixture of (1R,3S,5R)-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid 3-chloro-2-fluoro-benzylamide trifluoroacetate (70.2 mg, 0.183 mmol), (3-carbamoyl-indol-1-yl)acetic acid [1016689-54-5] (40.0 mg, 0.183 mmol), HBTU (104 mg, 0.275 mmol) and DIPEA (0.128 mL, 0.733 mmol) in CH2Cl2 (8 mL) was stirred at RT over 60 h. The reaction mixture was then diluted with CH2Cl2, and the solution was washed twice with 0.1N HCl. The precipitate formed in the aqueous layer was filtered off, washed with CH2Cl2 and dried in vacuo to afford the title product as a white solid. MS (LC/MS): 469 [M+H]+, 491 [M+Na]+; tR (HPLC conditions b): 3.56 min.

Workup

  1. washthe solution was washed twice with 0.1N HCl
  2. customThe precipitate formed in the aqueous layer
  3. filtrationwas filtered off
  4. washwashed with CH2Cl2
  5. customdried in vacuo

Sources & evidence

ORD record
ord-613bee7fe8e74bd98e1bd741ea79c6de
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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