Methanol → HCID 87315741, compound

HRID 1848854Notes

Reaction equation

HRID 1848854 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:56]=[CH:57][CH:58]=1)[O:5][C:6]1[CH:33]=[C:32]([N:34]2[CH2:39][CH2:38][N:37]([CH2:40][C:41]3[CH2:46][CH2:45][C:44]([CH3:48])([CH3:47])[CH2:43][C:42]=3[C:49]3[CH:54]=[CH:53][C:52]([Cl:55])=[CH:51][CH:50]=3)[CH2:36][CH2:35]2)[CH:31]=[CH:30][C:7]=1[C:8]([NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[C:16]([N+:27]([O-:29])=[O:28])[CH:15]=1)(=[O:13])=[O:12])=[O:9].[CH:59]1([CH:62]=O)[CH2:61][CH2:60]1.CO>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:56]=[CH:57][CH:58]=1)[O:5][C:6]1[CH:33]=[C:32]([N:34]2[CH2:39][CH2:38][N:37]([CH2:40][C:41]3[CH2:46][CH2:45][C:44]([CH3:48])([CH3:47])[CH2:43][C:42]=3[C:49]3[CH:50]=[CH:51][C:52]([Cl:55])=[CH:53][CH:54]=3)[CH2:36][CH2:35]2)[CH:31]=[CH:30][C:7]=1[C:8]([NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][CH:21]2[CH2:26][CH2:25][N:24]([CH2:62][CH:59]3[CH2:61][CH2:60]3)[CH2:23][CH2:22]2)=[C:16]([N+:27]([O-:29])=[O:28])[CH:15]=1)(=[O:12])=[O:13])=[O:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 123114CyclopropanecarboxaldehydeHCID 67228210HCID 67228210, compound

Product 1

HCID 87315741HCID 87315741, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of EXAMPLE 187B (50 mg), cyclopropanecarbaldehyde (100 mg) and MP-CNBH3 resin (0.2 g, 2.43 mmol/g) in dichloromethane (4 mL)/methanol (3 mL) was shaken for 16 hours at room temperature. The product was filtered, washed with dichloromethane/methanol and concentrated. The crude product was purified by RP HPLC (C8, 30%-100% CH3CN/water/0.1% TFA) to yield the product. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ 8.35 (s, 1H), 8.10 (s, 1H), 7.67-7.75 (m, 1H), 7.60 (d, 1H), 7.36 (d, 2H), 7.15 (t, 1H), 7.07 (d, 3H), 6.89 (d, 1H), 6.73 (dd, 1H), 6.63 (s, 1H), 6.60 (s, 1H), 6.40 (s, 1H), 3.86 (s, 1H), 3.12 (s, 5H), 2.71-2.80 (m, 3H), 2.13-2.28 (m, 9H), 1.98 (s, 3H), 1.79 (s, 1H), 1.41 (t, 2H), 0.99-1.11 (m, 2H), 0.94 (s, 6H), 0.84 (d, 1H), 0.63 (d, 2H), 0.33 (s, 2H).

Workup

  1. filtrationThe product was filtered
  2. washwashed with dichloromethane/methanol
  3. concentrationconcentrated
  4. customThe crude product was purified by RP HPLC (C8, 30%-100% CH3CN/water/0.1% TFA)
  5. customto yield the product

Sources & evidence

ORD record
ord-8f95e8eef64a40d990ca82879a958acb
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

Loading…