Cyclobutylamine → HCID 86714382, compound

HRID 1750170Notes

Reaction equation

HRID 1750170 reaction equation
[CH:1]1([NH2:5])[CH2:4][CH2:3][CH2:2]1.C1C=NC2N(O)N=NC=2C=1.[CH2:16]([CH:18]([N:21]1[C:25]2[CH:26]=[CH:27][C:28]([C:30]([NH:32][C@@H:33]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:34](O)=[O:35])=[O:31])=[CH:29][C:24]=2[N:23]=[C:22]1[CH2:41][C:42]1[S:43][CH:44]=[CH:45][CH:46]=1)[CH2:19][CH3:20])[CH3:17].CCN(C(C)C)C(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:1]1([NH:5][C:34]([C@@H:33]([NH:32][C:30]([C:28]2[CH:27]=[CH:26][C:25]3[N:21]([CH:18]([CH2:19][CH3:20])[CH2:16][CH3:17])[C:22]([CH2:41][C:42]4[S:43][CH:44]=[CH:45][CH:46]=4)=[N:23][C:24]=3[CH:29]=2)=[O:31])[CH2:37][CH:38]([CH3:39])[CH3:40])=[O:35])[CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 75645CyclobutylamineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 2733179PyBroPHCID 73442765HCID 73442765, compound

Product 1

HCID 86714382HCID 86714382, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Into a reaction vial were placed 10 mg of cyclobutylamine, 20 mg of HOAt, 53 mg of (S)-2-{[1-(1-Ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carbonyl]-amino}-4-methyl-pentanoic acid. Then 0.11 ml DIPEA in 1 ml DMF were added, followed by 67 mg PyBrOP in 0.5 ml DMF. The reaction was shaken at RT over night, then filtered and purified by HPLC to yield 39 mg (74%) of 1-(1-ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid ((S)-1-cyclobutylcarbamoyl-3-methyl-butyl)-amide.

Workup

  1. filtrationfiltered
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-6c80d345d79d41479ff43407a3291e94
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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