Methanol → HCID 60198781, compound

HRID 2279564Notes

Reaction equation

HRID 2279564 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([NH:22][C:23]([N:25]3[CH2:34][CH2:33][C:32]4[CH:31]=[N:30][C:29]([NH:35][CH:36]([CH3:38])[CH3:37])=[N:28][C:27]=4[CH2:26]3)=[O:24])[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].CO.O1CCOCC1.Cl>C(Cl)Cl.CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([NH:22][C:23]([N:25]3[CH2:34][CH2:33][C:32]4[CH:31]=[N:30][C:29]([NH:35][CH:36]([CH3:38])[CH3:37])=[N:28][C:27]=4[CH2:26]3)=[O:24])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 887MethanolHCID 204431481,4-Dioxane hydrochlorideHCID 86705549HCID 86705549, compound

Product 1

HCID 60198781HCID 60198781, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 362 (102 mg, 0.1810 mmol) in DCM (1.8 mL) at RT in a capped flask was added MeOH (180 μL) followed by 4M HCl dioxane solution (452.5 μL, 1.810 mmol). After 2 h the reaction was diluted with Et2O (5 mL) which produced a coarse yellow precipitate. The solid was filtered off and washed with generous amounts of ether to afford 80 mg (80%) of I-93 as a pale yellow solid which was dried under high vacuum: MS m/z (APCI-pos) M+1=463.4.

Workup

  1. customproduced a coarse yellow precipitate
  2. filtrationThe solid was filtered off
  3. washwashed with generous amounts of ether
  4. customto afford 80 mg (80%) of I-93 as a pale yellow solid which
  5. customwas dried under high vacuum

Sources & evidence

ORD record
ord-9f1a970bb8fd48c4a81aceafbe11e9c3
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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