Diisopropylethylamine → Morpholine-4-carboxylic acid [(S)-1-(1-cyano-cyclopropylcarbamoyl)-3,3-difluoro-hexyl]-amide

HRID 1455609Notes

Reaction equation

HRID 1455609 reaction equation
[F:1][C:2]([F:20])([CH2:17][CH2:18][CH3:19])[CH2:3][C@H:4]([NH:8][C:9]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:10])[C:5]([OH:7])=O.Cl.[NH2:22][C:23]1([C:26]#[N:27])[CH2:25][CH2:24]1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(N(C(C)C)CC)(C)C>>[C:26]([C:23]1([NH:22][C:5]([C@@H:4]([NH:8][C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[O:10])[CH2:3][C:2]([F:1])([F:20])[CH2:17][CH2:18][CH3:19])=[O:7])[CH2:25][CH2:24]1)#[N:27]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 145863631-Amino-1-cyclopropanecarbonitrile hydrochlorideHCID 57535361(S)-4,4-difluoro-2-[(morpholine-4-carbonyl)-amino]-heptanoic acid

Product 1

HCID 11485129Morpholine-4-carboxylic acid [(S)-1-(1-cyano-cyclopropylcarbamoyl)-3,3-difluoro-hexyl]-amide

Procedure

Prepared by reacting (S)-4,4-Difluoro-2-[(morpholine-4-carbonyl)-amino]-heptanoic acid and 1-Amino-cyclopropanecarbonitrile hydrochloride, using TOTU as the coupling agent and diisopropyl ethylamine as the base.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-8246fdcf3a854ffd844bfed8f2f7295a
Source dataset
uspto-grants-2009_01
Patent number
US07482448B2

Reaction notes

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