Ethyl chloroformate → HCID 70650988, compound

HRID 2361428Notes

Reaction equation

Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[CH3:7][C:8]1[C:13]([N:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[CH:15]2)=[CH:12][CH:11]=[CH:10][C:9]=1[C:25]1[CH:33]=[CH:32][C:31]([C:34]([NH2:36])=[O:35])=[C:30]2[C:26]=1[C:27]1[CH2:40][NH:39][CH2:38][CH2:37][C:28]=1[NH:29]2>>[C:34]([C:31]1[C:30]2[NH:29][C:28]3[CH2:37][CH2:38][N:39]([C:2]([O:4][CH2:5][CH3:6])=[O:3])[CH2:40][C:27]=3[C:26]=2[C:25]([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([N:14]3[C:23](=[O:24])[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]=[CH:15]3)[C:8]=2[CH3:7])=[CH:33][CH:32]=1)(=[O:35])[NH2:36]

Participants

Reactant 2

HCID 10928Ethyl chloroformate

HCID 67994842HCID 67994842, compound

Product 1

HCID 70650988HCID 70650988, compoundYield 59%

Procedure

Using the procedure of Example 43 but substituting ethyl chloroformate in place of acetic anhydride, 9-(2-methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-6-carboxamide (20 mg, 0.044 mmol) was converted into the desired product as a white solid (14.0 mg, 59% yield). LCMS (M+H)+ m/z 522.3. 1H NMR (400 MHz, methanol-d4) δ 8.16-8.56 (2 H, m), 7.87-7.98 (1 H, m), 7.76-7.87 (1 H, m), 7.61-7.73 (2 H, m), 7.42-7.59 (3 H, m), 6.89-7.06 (1 H, m), 3.42-4.22 (6 H, m), 2.79-3.01 (2 H, m), 1.86 (3 H, br. s.), 1.12-1.36 (3 H, m).

Sources & evidence

ORD record: ord-2a3bfa8ff9c443a4b56799626e2b68b2
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685969B2

Reaction notes

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