Acetic Acid → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(3-(4-isopropylpiperazin-1-yl)phenyl)-5-methylbenzo[d]thiazol-6-yl)acetic acid

HRID 879628ノート

反応式

HRID 879628 の反応式
[C:1]([O:5][C@@H:6]([C:10]1[C:30]([CH3:31])=[CH:29][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:39][C:40]([CH3:42])=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.O>[C:1]([O:5][C@@H:6]([C:10]1[C:30]([CH3:31])=[CH:29][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N:23]4[CH2:28][CH2:27][N:26]([CH:40]([CH3:42])[CH3:39])[CH2:25][CH2:24]4)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:32]1[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 86700437(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(piperazin-1-yl)phenyl)benzo[d]thiazol-6-yl)acetic acid

生成物 1

HCID 86700438(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(3-(4-isopropylpiperazin-1-yl)phenyl)-5-methylbenzo[d]thiazol-6-yl)acetic acid

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a solution of (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(piperazin-1-yl)phenyl)benzo[d]thiazol-6-yl)acetic acid (30 mg, 0.055 mmol) in MeOH (1 mL) was added acetone (0.20 mL), acetic acid (0.08 mL), and sodium triacetoxyborohydride (58 mg, 0.27 mmol). Stirred at rt for 18 h then 60° C. for 3 h (reaction not to completion). H2O added (1 mL) and purified using reverse phase HPLC, eluting by 2-100% acetonitrile in H2O with 0.1% TFA to give the product. 1H NMR (400 MHz, CD3OD) δ 7.83 (s, 1H), 7.68 (m, 2H), 7.58 (m, 3H), 7.43 (t, J=8 Hz, 1H), 7.21 (d, J=8 Hz, 1H), 5.25 (s, 1H), 4.02 (m, 2H), 3.60 (m, 4H), 3.12 (m, 3H), 2.61 (s, 3H), 1.43 (d, J=7 Hz, 6H), 0.97 (s, 9H). LCMS-ESI+: calc'd for C33H39ClN3O3S: 592.2 (M+H+); Found: 592.3 (M+H+).

後処理

  1. custom60° C. for 3 h (reaction not to completion)
  2. custompurified
  3. washeluting by 2-100% acetonitrile in H2O with 0.1% TFA
  4. customto give the product

出典と根拠

ORDレコード
ord-0477f670ef80479faadd1b94414956ee
出典データセット
uspto-grants-2015_03
特許番号
US08987250B2

反応ノート

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