2,6-Di-tert-butyl-4-methylpyridine → [(1R,2S,4R)-4-({6-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}-amino)-2-hydroxycyclopentyl]methyl sulfamate

HRID 1677925노트

반응식

HRID 1677925 반응식
[C@@H:1]1([NH:10][C:11]2[N:16]=[CH:15][N:14]=[C:13]([NH:17][C@H:18]3[CH2:22][C@H:21]([OH:23])[C@@H:20]([CH2:24][OH:25])[CH2:19]3)[CH:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C.Cl[S:42]([NH:45]C(=O)OC(C)(C)C)(=[O:44])=[O:43]>C(#N)C>[S:42](=[O:44])(=[O:43])([O:25][CH2:24][C@H:20]1[CH2:19][C@@H:18]([NH:17][C:13]2[CH:12]=[C:11]([NH:10][C@@H:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:3][CH2:2]3)[N:16]=[CH:15][N:14]=2)[CH2:22][C@@H:21]1[OH:23])[NH2:45]

참가 물질

5

반응물 3

HCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 15677406tert-butyl N-(chlorosulfonyl)carbamateHCID 66797896(1S,2R,4R)-4-({6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}amino)-2-(hydroxymethyl)cyclopentanol

생성물 1

HCID 24829705[(1R,2S,4R)-4-({6-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}-amino)-2-hydroxycyclopentyl]methyl sulfamate수율 40.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A neat mixture of (1S,2R,4R)-4-({6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}amino)-2-(hydroxymethyl)cyclopentanol (100. mg, 0.294 mmol) and 2,6-di-tert-butyl-4-methylpyridine (181 mg, 0.881 mmol) was dissolved in ACN (5.00 mL) before tert-butyl (chlorosulfonyl)carbamate (95.0 mg, 0.441 mmol, as prepared in Example 21c) was added. The reaction was stirred for 2 h before being quenched via addition of MeOH (2 mL). The resulting mixture was concentrated in vacuo and purified via silica gel chromatography eluting with a gradient of 10 to 20% MeOH in DCM to afford the title compound as an amorphous solid (50.0 mg, 33%). LC/MS: Rt=1.24 min, ES+ 520. (AA standard).

후처리

  1. additionwas added
  2. custombefore being quenched via addition of MeOH (2 mL)
  3. concentrationThe resulting mixture was concentrated in vacuo
  4. custompurified via silica gel chromatography
  5. washeluting with a gradient of 10 to 20% MeOH in DCM

출처 및 근거

ORD 기록
ord-4a05b46a9084475baa2cf3801c1bae45
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008307B2

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