Diisopropylethylamine → HCID 69307077, compound

HRID 1392202Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([C:16]([OH:18])=O)=[CH:11][CH:10]=3)=[CH:3][CH:2]=1.[NH2:19][CH:20]([CH2:24][S:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:21](O)=[O:22].F[P-](F)(F)(F)(F)F.[N:39]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C>CN(C=O)C>[C:21]([CH:20]([NH:19][C:16]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1)=[CH:15]2)=[O:18])[CH2:24][S:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:22])[NH2:39]

Participants

Conditions

Temperature: 20 °C

Procedure

0.20 g (0.84 mmol) of 2-pyridin-4-yl-1H-indole-5-carboxylic acid was admixed with 0.21 g (1.07 mmol) of 2-amino-3-phenylsulfanylpropionic acid in 40 ml of DMF and, at 0° C., 0.66 g (1.27 mmol) of benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate and 0.37 ml (2.12 mmol) of N-ethyl-N,N-diisopropylamine were added, and the solution was stirred at 20° C. for 2 h. The solution was concentrated under reduced pressure and purified by medium pressure column chromatography (CH2Cl2/CH3OH:9:1). This gave 0.19 g (54%) of N-(1-carbamoyl-2-phenylsulfanylethyl)-2-pyridin-4yl-1H-indole-5-carboxamide.

Workup

concentrationThe solution was concentrated under reduced pressure
custompurified by medium pressure column chromatography (CH2Cl2/CH3OH:9:1)

Sources & evidence

ORD record: ord-fde6d428b9c44538a627f5c23a09d19b
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342029B2

Reaction notes

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