2-Chlorothiazole-5-carbonitrile → (1-Carbamoyl-4-adamantyl) 3-(5-cyanothiazol-2-ylamino)pyrrolidine-1-carboxylate

HRID 72140Notes

Reaction equation

HRID 72140 reaction equation
C(O[C:6]([NH:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH:17]2[CH:24]3[CH2:25][C:20]4([C:27](=[O:29])[NH2:28])[CH2:21][CH:22]([CH2:26][CH:18]2[CH2:19]4)[CH2:23]3)=[O:15])[CH2:10]1)=O)(C)(C)C.ClC1[S:32][C:33]([C:36]#[N:37])=[CH:34][N:35]=1>>[C:36]([C:33]1[S:32][C:6]([NH:8][CH:9]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH:17]3[CH:24]4[CH2:25][C:20]5([C:27](=[O:29])[NH2:28])[CH2:21][CH:22]([CH2:26][CH:18]3[CH2:19]5)[CH2:23]4)=[O:15])[CH2:10]2)=[N:35][CH:34]=1)#[N:37]

Participants

3

Reactant 2

HCID 14852222-Chlorothiazole-5-carbonitrileHCID 75968129(1-Carbamoyl-4-adamantyl) 3-(tert-butoxycarbonylamino)pyrrolidine-1-carboxylate

Product 1

HCID 86653267(1-Carbamoyl-4-adamantyl) 3-(5-cyanothiazol-2-ylamino)pyrrolidine-1-carboxylate

Procedure

The title compound was prepared from (3R) (1-carbamoyl-4-adamantyl) 3-(tert-butoxycarbonylamino)pyrrolidine-1-carboxylate isomer 2 following procedures analogous to those described in Example 33 using 2-chloro-5-cyanothiazole in Step 2. LC-MS Method 1 tR=1.32 min, m/z=415; 1H NMR (CD3OD) 1.55 (2H), 1.85-2.15 (12H), 2.25 (m, 1H), 3.35-3.80 (4H), 4.40 (br s, 1H), 4.78 (s, 1H), 7.74 (s, 1H).

Sources & evidence

ORD record
ord-ff60ca94aad7434ab53681e39129bd8e
Source dataset
uspto-grants-2014_09
Patent number
US08828985B2

Reaction notes

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