2-Chloro-6-methoxybenzothiazole → HCID 68999293, compound

HRID 750047Notes

Reaction equation

HRID 750047 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:23]1[S:24][C:25]2[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:26]=2[N:27]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:23]2[S:24][C:25]3[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:26]=3[N:27]=2)=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 2731322-Chloro-6-methoxybenzothiazoleHCID 68999591(R)-2-(4-Hydroxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68999293HCID 68999293, compoundYield 77%

Procedure

Followed the same procedure as that of step 1 in Example 99 with the use of (R)-2-(4-hydroxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester ((147 mg, 0.5 mmol) and 2-chloro-6-methoxy-benzothiazole (100 mg, 0.5 mmol) to afford the title product (185 mg, 77% yield); 1H NMR (400 MHz, CDCl3); δ 1.46 (s, 9H), 1.80-2.10 (m, 4H), 3.28-3.46 (m, 2H), 3.70-3.98 (m, 1H), 3.84 (s, 3H), 4.01-4.20 (m, 2H), 6.72-6.82 (m, 4H), 6.92-6.99 (m, 2H), 7.62 (d, J=8.8 Hz, 1H).

Sources & evidence

ORD record
ord-96293c9ae9cd4bc6a8a04026ce3f07d4
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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