N,N-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chromane-2-carboxamide → HCID 178493465, compound

HRID 1778652Notes

Reaction equation

HRID 1778652 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[N:18]=[C:17]2[NH:19][N:20]=[C:21](I)[C:16]2=[CH:15][N:14]=1.[CH3:23][N:24]([CH3:46])[C:25]([CH:27]1[CH2:36][CH2:35][C:34]2[C:29](=[CH:30][CH:31]=[C:32](B3OC(C)(C)C(C)(C)O3)[CH:33]=2)[O:28]1)=[O:26]>>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[N:18]=[C:17]2[NH:19][N:20]=[C:21]([C:32]3[CH:33]=[C:34]4[C:29](=[CH:30][CH:31]=3)[O:28][CH:27]([C:25]([N:24]([CH3:46])[CH3:23])=[O:26])[CH2:36][CH2:35]4)[C:16]2=[CH:15][N:14]=1

Participants

3

Reactant 2

HCID 86722804N,N-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chromane-2-carboxamideHCID 178493476HCID 178493476, compound

Product 1

HCID 178493465HCID 178493465, compound

Procedure

This compound was prepared by using procedures analogous to those described for the synthesis of Example 1, Step 7 starting from 6-(2,6-dichloro-3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidine and N,N-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chromane-2-carboxamide. LCMS (M+H)+=528.0/530.0. 1H NMR (300 MHz, DMSO-d6) δ: 9.77 (s, 1H), 7.87 (s, 1H), 7.85 (d, J=9.1 Hz, 1H), 7.06 (s, 1H), 6.95 (d, J=9.1 Hz, 1H), 5.19-5.14 (m, 1H), 3.99 (s, 6H), 3.12 (s, 3H), 2.89 (s, 3H), 2.15-1.95 (m, 4H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-389ffec3a9a54428a7ded6e488f43f9e
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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