Hydrochloric Acid → Formate

HRID 1514290Notes

Reaction equation

HRID 1514290 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:35]=[CH:34][C:21]4[CH2:22][CH2:23][N:24]([C:27]([O:29]C(C)(C)C)=[O:28])[CH2:25][CH2:26][C:20]=4[CH:19]=3)[N:14]=2)[CH:6]=[N:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].Cl.O1CCOCC1>ClCCl>[CH:27]([OH:29])=[O:28].[CH3:12][CH:10]([O:9][C:8]1[C:3]([C:1]#[N:2])=[CH:4][C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:35]=[CH:34][C:21]4[CH2:22][CH2:23][NH:24][CH2:25][CH2:26][C:20]=4[CH:19]=3)[N:14]=2)=[CH:6][N:7]=1)[CH3:11].[CH:27]([O-:29])=[O:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57505922HCID 57505922, compound

Product 2

HCID 283FormateYield 518.8%HCID 44129292HCID 44129292, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl 7-(5-{5-cyano-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (Preparation 95) (224 mg, 0.471 mmol) in dichloromethane (1 ml) was treated with 4M HCl in dioxan (5 ml, 20.0 mmol). The colourless solution was left at room temperature over the week-end to give a colourless precipitate. The reaction mixture was concentrated, triturated with ether and dried. The crude product was treated with DMSO:MeOH (1:1; 1.9 ml), the mixture filtered and the filtrate purified by MDAP. The title compound was obtained as a formate salt (55 mgs), δH (400 MHz, d6DMSO), 1.41 (6H, d), 3.07-3.20 (4H, m), 5.51 (1H, m), 7.42 (1H, d), 7.88 (1H dd), 7.91 (1H, d), 8.24 (1H, s), 8.98 (1H, d) and 9.20 (1H, d); MS (ES) C21H21N5O2 requires 375; found 376[M+H]+.

Workup

  1. waitThe colourless solution was left at room temperature over the week-end
  2. customto give a colourless precipitate
  3. concentrationThe reaction mixture was concentrated
  4. customtriturated with ether
  5. customdried
  6. additionThe crude product was treated with DMSO:MeOH (1:1; 1.9 ml)
  7. filtrationthe mixture filtered
  8. customthe filtrate purified by MDAP

Sources & evidence

ORD record
ord-018a7b4a40114b0c92724cd2c12e9821
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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