Acetic Acid → HCID 86700324, compound

HRID 879504Notes

Reaction equation

HRID 879504 reaction equation
[C:1]([O:5][C@@H:6]([C:10]1[C:35]([CH3:36])=[CH:34][C:13]2[N:14]=[C:15]([N:17]3[CH2:22][CH2:21][NH:20][CH:19]([C:23]4[CH:24]=[C:25]5[C:29](=[CH:30][CH:31]=4)[N:28]([CH3:32])[N:27]=[CH:26]5)[C:18]3=[O:33])[S:16][C:12]=2[C:11]=1[C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].C=O.[C:46](O)(=O)C.C([BH3-])#N.[Na+]>CO>[C:1]([O:5][C@@H:6]([C:10]1[C:35]([CH3:36])=[CH:34][C:13]2[N:14]=[C:15]([N:17]3[CH2:22][CH2:21][N:20]([CH3:46])[CH:19]([C:23]4[CH:24]=[C:25]5[C:29](=[CH:30][CH:31]=4)[N:28]([CH3:32])[N:27]=[CH:26]5)[C:18]3=[O:33])[S:16][C:12]=2[C:11]=1[C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86700322HCID 86700322, compound

Product 1

HCID 86700324HCID 86700324, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of: (2S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)-2-oxopiperazin-1-yl)benzo[d]thiazol-6-yl)acetic acid (3 mg) in methanol (0.5 mL) was added formaldehyde solution (20 μL, 37%), followed by acetic acid (10 μL) and sodium cyanoborohydride (12 mg). The mixture was stirred for 1 hour, and solvents were removed under reduced pressure. The remaining solid was dissolved with DMF/water (1 mL/0.5 mL), and was purified with reverse phase HPLC to give (2S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(4-methyl-3-(1-methyl-1H-indazol-5-yl)-2-oxopiperazin-1-yl)benzo[d]thiazol-6-yl)acetic acid. LCMS-ESI+: calc'd for C33H35ClN5O4S: 632.2 (M+H+); Found: 632.2 (M+H+). 1H-NMR 400 MHz, (CD3OD) δ 8.0 (m, 1H), 7.82 (m, 1H), 7.68 (s, 1H), 7.62-7.40 (m, 6H), 5.21 (m, 1H), 4.70 (m, 1H), 4.6-4.3 (m, 2H), 4.08/4.05 (s, 3H), 3.5 (m, 2H), 2.57 (s, 3H), 2.40 (m, 3H), 0.93 (s, 9H).

Workup

  1. customsolvents were removed under reduced pressure
  2. dissolutionThe remaining solid was dissolved with DMF/water (1 mL/0.5 mL)
  3. customwas purified with reverse phase HPLC

Sources & evidence

ORD record
ord-cb5f3426e74c4b4fb65db5c2e44fe27a
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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