Hydrochloric Acid → HCID 59190355, compound

HRID 1684935Notes

Reaction equation

[C:1]1([C:7]2[NH:17][C:10]3=[N:11][CH:12]=[C:13]([C:15]#[N:16])[CH:14]=[C:9]3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:18]=O.[NH:20]1[CH2:25][CH2:24][CH:23]([NH:26]C(=O)OC(C)(C)C)[CH2:22][CH2:21]1.Cl>C(O)(=O)C>[NH2:26][CH:23]1[CH2:22][CH2:21][N:20]([CH2:18][C:8]2[C:9]3[C:10](=[N:11][CH:12]=[C:13]([C:15]#[N:16])[CH:14]=3)[NH:17][C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:25][CH2:24]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of the compound prepared in Example 9 (22 mg, 0.1 mmol) in acetic acid (1 mL) were added formalin (0.1 mL) and tert-butyl piperidin-4-ylcarbamate (30 mg, 0.5 mmol). The reaction mixture was stirred at 80° C. for 1 h. The LC/MS showed a peak of m/e=462. Aqueous HCl (3N, 1 mL) was added and the resulting mixture was heated to 100° C. for 4 h. The LC/LC/MS; (M+H)+=analysis indicated the formation of the desired product. The mixture was cooled, concentrated and the residue was purified by preparative RP HPLC eluting with a mixture of methanol in water containing 0.1% TFA. The fractions containing the desired product were collected, concentrated and converted to HCl salt to afford the title compound (40 mg) as a solid. LC/MS; (M+H)+=332.

Workup

temperaturethe resulting mixture was heated to 100° C. for 4 h

Sources & evidence

ORD record: ord-b529c07315fc489bbedb34140345c9cc
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148361B2

Reaction notes

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