Formaldehyde → HCID 67441954, compound

HRID 624375Notes

Reaction equation

HRID 624375 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:55]=[CH:56][CH:57]=1)[O:5][C:6]1[CH:32]=[C:31]([N:33]2[CH2:38][CH2:37][N:36]([CH2:39][C:40]3[CH2:45][CH2:44][C:43]([CH3:47])([CH3:46])[CH2:42][C:41]=3[C:48]3[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][CH:49]=3)[CH2:35][CH2:34]2)[CH:30]=[CH:29][C:7]=1[C:8]([NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C@H:21]2[CH2:25][CH2:24][NH:23][CH2:22]2)=[C:16]([N+:26]([O-:28])=[O:27])[CH:15]=1)(=[O:13])=[O:12])=[O:9].[CH2:58]=O>O1CCCC1.C(O)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:55]=[CH:56][CH:57]=1)[O:5][C:6]1[CH:32]=[C:31]([N:33]2[CH2:34][CH2:35][N:36]([CH2:39][C:40]3[CH2:45][CH2:44][C:43]([CH3:47])([CH3:46])[CH2:42][C:41]=3[C:48]3[CH:49]=[CH:50][C:51]([Cl:54])=[CH:52][CH:53]=3)[CH2:37][CH2:38]2)[CH:30]=[CH:29][C:7]=1[C:8]([NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C@H:21]2[CH2:25][CH2:24][N:23]([CH3:58])[CH2:22]2)=[C:16]([N+:26]([O-:28])=[O:27])[CH:15]=1)(=[O:12])=[O:13])=[O:9]

Participants

6

Reactant 2

HCID 712FormaldehydeHCID 67431027HCID 67431027, compound

Product 1

HCID 67441954HCID 67441954, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 194C (470 mg) in tetrahydrofuran (3 mL) and acetic acid (1 mL) was added 37% formaldehyde solution in water (0.42 mL) and MP-CNBH3 resin (947 mg, 2.38 mmol/g)). The reaction mixture was stirred overnight at room temperature. The resin was filtered off and reaction mixture was then concentrated. The residue was purified by flash chromatography, eluting with ethyl acetate, followed by a gradient of 3-10% methanol/dichloromethane. 1H NMR (500 MHz, dimethylsulfoxide-d6) δ 8.42 (d, 1H), 8.34 (m, 1H), 7.78 (dd, 1H), 7.53 (d, 1H), 7.36 (d, 2H), 7.19 (t, 1H), 7.08 (m, 3H), 6.95 (m, 1H), 6.76 (dd, 1H), 6.67 (m, 2H), 6.45 (d, 1H), 3.53 (m, 2H), 3.16 (m, 7H), 2.83 (m, 4H), 2.61 (br m, 1H), 2.27 (m, 4H), 2.18 (m, 3H), 1.98 (m, 3H), 1.41 (m, 2H), 0.94 (s, 6H).

Workup

  1. filtrationThe resin was filtered off
  2. customreaction mixture
  3. concentrationwas then concentrated
  4. customThe residue was purified by flash chromatography
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-b84cc123128346289ef6b7cdf12369c5
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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