Triethylamine hydrochloride → HCID 178519789, compound

HRID 1772589Notes

Reaction equation

[OH:1][CH2:2][C:3]1[N:4]=[C:5]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[N:9][CH:8]=[C:7]([C:17]3[CH:18]=[CH:19][C:20]([C:23]#[N:24])=[N:21][CH:22]=3)[N:6]2[CH:25]=1.[N-:26]=[N+:27]=[N-:28].[Na+].Cl.C(N(CC)CC)C>CN(C=O)C>[NH:26]1[C:23]([C:20]2[N:21]=[CH:22][C:17]([C:7]3[N:6]4[CH:25]=[C:3]([CH2:2][OH:1])[N:4]=[C:5]4[C:10]([N:11]4[CH2:16][CH2:15][O:14][CH2:13][CH2:12]4)=[N:9][CH:8]=3)=[CH:18][CH:19]=2)=[N:24][N:28]=[N:27]1

Participants

Conditions

Temperature: 105 °C

Procedure

To a solution of compound 1g (220 mg, 0.650 mmol) in DMF (15 mL) was added NaN3 (440 mg, 6.77 mmol) and triethylamine hydrochloride (440 mg, 3.21 mmol). The reaction mixture was stirred at 105° C. for 1 h. The resulting mixture was concentrated, and diluted with H2O (30 mL). The solids were collected by filtration and washed with Et2O to obtain compound 1h as a yellow solid (189 mg, 76% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C17H17N9O2: 380.2 (M+H). Found 380.2.

Workup

concentrationThe resulting mixture was concentrated
additiondiluted with H2O (30 mL)
filtrationThe solids were collected by filtration
washwashed with Et2O

Sources & evidence

ORD record: ord-6b7c3524ee394f5aaa9e879677e54abe
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249163B2

Reaction notes

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