Formic Acid → {(S)-3-[(6-Chloro-benzooxazol-2-ylamino)-methyl]-pyrrolidin-1-yl}-(2,6-dimethoxy-phenyl)-methanone

HRID 222417

반응식

HRID 222417 반응식
Cl.[Cl:2][C:3]1[CH:18]=[CH:17][C:6]2[N:7]=[C:8]([NH:10][CH2:11][C@@H:12]3[CH2:16][CH2:15][NH:14][CH2:13]3)[O:9][C:5]=2[CH:4]=1.[CH3:19][O:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[C:22]=1[C:23](O)=[O:24].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(O)=O>CN(C=O)C.CCN(C(C)C)C(C)C>[Cl:2][C:3]1[CH:18]=[CH:17][C:6]2[N:7]=[C:8]([NH:10][CH2:11][C@@H:12]3[CH2:16][CH2:15][N:14]([C:23]([C:22]4[C:26]([O:30][CH3:31])=[CH:27][CH:28]=[CH:29][C:21]=4[O:20][CH3:19])=[O:24])[CH2:13]3)[O:9][C:5]=2[CH:4]=1

참가 물질

7

반응물 4

HCID 284Formic AcidHCID 151092,6-Dimethoxybenzoic AcidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 131728778(6-Chloro-benzooxazol-2-yl)-(R)-1-pyrrolidin-3-ylmethyl-amine, hydrochloride2회

생성물 1

HCID 44628353{(S)-3-[(6-Chloro-benzooxazol-2-ylamino)-methyl]-pyrrolidin-1-yl}-(2,6-dimethoxy-phenyl)-methanone수율 38.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 81531Diisopropylethylamine용매

실험 절차

A mixture of 146.3 mg (0.45 mmol) (6-chloro-benzooxazol-2-yl)-(R)-1-pyrrolidin-3-ylmethyl-amine, hydrochloride (intermediate 1), 106.7 mg (0.586 mmol) 2,6-dimethoxy-benzoic acid (commercially available) and 206.9 mg (0.64 mmol) TBTU in 4 mL DMF and 0.3 mL DIPEA was shaken at room temperature over night. The mixture was acidified with formic acid and subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid. The product containing fractions were evaporated to yield 72 mg (38%) of the title compound. MS (m/e): 416.2 (MH+).

후처리

  1. customsubjected to purification by preparative HPLC on reversed phase
  2. washeluting with a gradient
  3. customformed from acetonitrile, water and formic acid
  4. additionThe product containing fractions
  5. customwere evaporated

출처 및 근거

ORD 기록
ord-50e5193ec4c644509b3b0a3bc1e135c5
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207220B2

연결된 노트

불러오는 중…