HCID 53629224, compound → HCID 58091491, compound

HRID 1874013Notes

Reaction equation

HRID 1874013 reaction equation
[CH3:1][C:2]([C@@H:13]1[C:22]2[C:17](=[N:18][C:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)=[O:30])=[CH:25][CH:24]=3)=[CH:20][CH:21]=2)[O:16][C:15]2[N:37]=[C:38]([CH3:41])[CH:39]=[CH:40][C:14]1=2)([CH3:12])[C:3]([NH:5][C:6]1N=N[N:9](C)[N:10]=1)=[O:4].NN1NC=[C:45]([CH:48]2[CH2:50][CH2:49]2)[S:44]1>>[CH:48]1([C:45]2[S:44][C:6]([NH:5][C:3](=[O:4])[C:2]([CH3:1])([C@@H:13]3[C:22]4[C:17](=[N:18][C:19]([C:23]5[CH:24]=[CH:25][C:26]([C:29]([N:31]6[CH2:36][CH2:35][O:34][CH2:33][CH2:32]6)=[O:30])=[CH:27][CH:28]=5)=[CH:20][CH:21]=4)[O:16][C:15]4[N:37]=[C:38]([CH3:41])[CH:39]=[CH:40][C:14]3=4)[CH3:12])=[N:10][N:9]=2)[CH2:49][CH2:50]1

Participants

3

Reactant 2

HCID 53629224HCID 53629224, compoundHCID 58091566HCID 58091566, compound

Product 1

HCID 58091491HCID 58091491, compound

Procedure

Following conditions described for Step 9 of Example 14, the acid from Step 1 of Example 92 was coupled with 2-amino-5-cyclopropylthiadiazole to give Example 93. 1H NMR (400 MHz, chloroform-d) δ ppm 1.16-1.41 (m, 10H) 2.27-2.38 (m, 1H) 2.57 (s, 3H) 3.43-3.93 (m, 8H) 4.59 (s, 1H) 7.01 (d, J=7.78 Hz, 1H) 7.51 (t, J=8.53 Hz, 3H) 7.56-7.67 (m, 2H) 8.12 (d, 2H); MS (ES+) m/z: 597 (M+H); LC retention time: 3.08 min (analytical HPLC Method B).

Workup

  1. customto give Example 93

Sources & evidence

ORD record
ord-c2c488efd4dc48f086a5c90b84a5c788
Source dataset
uspto-grants-2012_11
Patent number
US08304539B2

Reaction notes

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