1-Hydroxybenzotriazole → HCID 49842383, compound

HRID 1615775Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH:12]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)[N:11]([CH2:22][C:23](O)=[O:24])[C:10](=[O:26])[C@@H:9]1[CH2:27][CH:28]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)=O)(C)(C)C.[NH2:35][C:36]1[CH:37]=[C:38]2[C:51](=[CH:52][CH:53]=1)[CH2:50][C@:40]1([C:48]3[C:43](=[N:44][CH:45]=[CH:46][CH:47]=3)[NH:42][C:41]1=[O:49])[CH2:39]2.Cl.C(N=C=NCCCN(C)C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH:28]1([CH2:27][C@@H:9]2[NH:8][CH2:13][CH:12]([C:14]3[CH:15]=[C:16]([F:21])[CH:17]=[C:18]([F:20])[CH:19]=3)[N:11]([CH2:22][C:23]([NH:35][C:36]3[CH:37]=[C:38]4[C:51](=[CH:52][CH:53]=3)[CH2:50][C@:40]3([C:48]5[C:43](=[N:44][CH:45]=[CH:46][CH:47]=5)[NH:42][C:41]3=[O:49])[CH2:39]4)=[O:24])[C:10]2=[O:26])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1

Participants

Conditions

Temperature: 50 °C

Procedure

100 mg (0.21 mmol) 2-((3S)-4-(tert-butoxycarbonyl)-3-(cycloheptylmethyl)-6-(3,5-difluorophenyl)-2-oxopiperazin-1-yl)ethanoic acid, 58 mg (0.23 mmol) (R)-5-amino-1,3-dihydrospiro[inden-2,3′-pyrrol[2,3-b]pyridin]-2′(1′H)-one, 56 mg (0.29 mmol) 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide-hydrochloride, 39 mg (0.29 mmol) HOBT, 0.03 ml (0.23 mmol) TEA and 1.50 ml DMF were stirred overnight at RT. The mixture was concentrated by rotary evaporation. The residue was combined with 15 ml of a 1.25M methanolic hydrochloric acid and stirred for 2 h at 50° C. The diastereomers were separated by RP-HPLC. The fractions containing the product were lyophilised.

Workup

concentrationThe mixture was concentrated by rotary evaporation
customThe diastereomers were separated by RP-HPLC
additionThe fractions containing the product

Sources & evidence

ORD record: ord-b086998e28244384bd9596f53cd74a8c
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765763B2

Reaction notes

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