tert-Butanol → HCID 69171435, compound

HRID 2114859Notes

Reaction equation

HRID 2114859 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[F:30])[CH2:5][N:6]1[CH:20]=[C:19](C(O)=O)[C:18]2[N:11]3[CH2:12][CH2:13][N:14]([CH3:17])[C:15](=[O:16])[C:10]3=[C:9]([O:24][CH3:25])[C:8]=2[C:7]1=[O:26].C([N:34]([CH:37](C)C)CC)(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:47])C=CC=CC=1.ClC1C=CC=CC=1Cl.[C:65]([OH:69])([CH3:68])([CH3:67])[CH3:66]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[F:30])[CH2:5][N:6]1[CH:20]=[C:19]([NH:34][C:37]([O:69][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:47])[C:18]2[N:11]3[CH2:12][CH2:13][N:14]([CH3:17])[C:15](=[O:16])[C:10]3=[C:9]([O:24][CH3:25])[C:8]=2[C:7]1=[O:26]

Participants

6

Reactant 5

HCID 6386tert-ButanolHCID 72391,2-DichlorobenzeneHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 69317721HCID 69317721, compound

Product 1

HCID 69171435HCID 69171435, compound

Conditions

Temperature
120 °C

Procedure

A solution of 2-(3-chloro-4-fluorobenzyl)-10-methoxy-8-methyl-1,9-dioxo-1,2,6,7,8,9-hexahydropyrido[3′,4′:4,5]pyrrolo[1,2-a]-pyrazine-4-carboxylic acid (0.74 g, 1.70 mmol), diisopropylethylamine (0.28 g, 2.13 mmol), and diphenylphosphoryl azide (0.57 g, 2.13 mmol) in mixture of 1,2-dichlorobenzene (10 mL) and anhydrous tert-butyl alcohol (10 mL) was heated in a sealed tube in an oil bath 120° C. for one hour. The reaction mixture was concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a methanol in ethyl acetate gradient. Collection and concentration of appropriate fractions provided the titled compound.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-7e91fdb01a9e4ea8883e7278f0dce7a7
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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