Pyrrolidine → HCID 58091584, compound

HRID 1874012Notes

Reaction equation

HRID 1874012 reaction equation
Cl[C:2]1[N:7]=[C:6]2[O:8][C:9]3[N:26]=[C:25]([C:27]4[CH:37]=[CH:36][C:30]([C:31]([N:33]([CH3:35])[CH3:34])=[O:32])=[CH:29][CH:28]=4)[CH:24]=[CH:23][C:10]=3[CH:11]([C:12]([CH3:22])([CH3:21])[C:13](=[O:20])[NH:14][C:15]3[S:16][CH:17]=[N:18][N:19]=3)[C:5]2=[CH:4][CH:3]=1.[NH:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1>>[CH3:21][C:12]([CH:11]1[C:5]2[C:6](=[N:7][C:2]([N:38]3[CH2:42][CH2:41][CH2:40][CH2:39]3)=[CH:3][CH:4]=2)[O:8][C:9]2[N:26]=[C:25]([C:27]3[CH:37]=[CH:36][C:30]([C:31]([N:33]([CH3:35])[CH3:34])=[O:32])=[CH:29][CH:28]=3)[CH:24]=[CH:23][C:10]1=2)([CH3:22])[C:13](=[O:20])[NH:14][C:15]1[S:16][CH:17]=[N:18][N:19]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 58091600HCID 58091600, compound

Product 1

HCID 58091584HCID 58091584, compound

Procedure

Using conditions described for synthesis of Example 67, the acid from Step 4 of Example 54 was reacted with pyrrolidine and converted Example 70. 1H NMR (400 MHz, chloroform-d) δ ppm 8.90 (1H, s), 8.06 (2H, d, J=8.31 Hz), 7.56 (2H, s), 7.51 (2H, d, J=8.31 Hz), 7.42 (1H, d, J=8.81 Hz), 6.27 (1H, d, J=8.56 Hz), 4.43 (1H, s), 3.53-3.64 (4H, m), 3.19 (3H, s), 3.06 (3H, s), 2.00-2.16 (4H, m), 1.25 (3H, s), 1.23 (3H, s); MS (ES+) m/z: 570 (M+H); LC retention time: 3.88 min (analytical HPLC Method A).

Workup

  1. customdescribed for synthesis of Example 67

Sources & evidence

ORD record
ord-1224707a5d534ef49c9ed7dbc84910e0
Source dataset
uspto-grants-2012_11
Patent number
US08304539B2

Reaction notes

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