1-(Oxetan-3-yl)piperazine → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(6-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-yl)benzo[d]thiazol-6-yl)acetic acid

HRID 879547Notes

Reaction equation

HRID 879547 reaction equation
[C:1]([O:5][C@@H:6]([C:10]1[C:33]([CH3:34])=[CH:32][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:29]([CH3:31])[CH3:30])[CH2:25][CH2:24]4)[N:18]=3)[S:16][C:12]=2[C:11]=1[C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].[O:42]1CC(N2CCNCC2)C1>>[C:1]([O:5][C@@H:6]([C:10]1[C:33]([CH3:34])=[CH:32][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:29]5[CH2:30][O:42][CH2:31]5)[CH2:25][CH2:24]4)[N:18]=3)[S:16][C:12]=2[C:11]=1[C:35]1[CH:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=1)[C:7]([OH:9])=[O:8])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 574162871-(Oxetan-3-yl)piperazineHCID 86700370(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(6-(4-isopropylpiperazin-1-yl)pyridin-2-yl)-5-methylbenzo[d]thiazol-6-yl)acetic acid

Product 1

HCID 72194233(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(6-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-yl)benzo[d]thiazol-6-yl)acetic acid

Procedure

(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(6-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-yl)benzo[d]thiazol-6-yl)acetic acid was prepared in a similar manner as (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(6-(4-isopropylpiperazin-1-yl)pyridin-2-yl)-5-methylbenzo[d]thiazol-6-yl)acetic acid, except using 1-(oxetan-3-yl)piperazine instead of 1-isopropylpiperazine. LCMS-ESI+: calc'd for C32H36ClN4O4S: 607.2 (M+H+); Found: 607.2 (M+H+); 1H NMR (400 MHz, CD3OD): δ 7.70-7.81 (m, 3H), 7.64 (m, 1H), 7.49-7.56 (m, 3H), 7.04 (d, J=8 Hz, 1H), 5.19 (s, 1H), 4.88 (br m, 2H), 4.77 (br m [under solvent], 4H), 4.35 (m, 1H), 3.80 (br m, 2H), 3.24 (m, [under solvent] 4H), 0.93 (s, 9H).

Sources & evidence

ORD record
ord-08ad3a91114d45a2993706b3e14d095b
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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