Dibutyltin oxide → HCID 178448270, compound

HRID 491900Notes

Reaction equation

[C:1]([CH:3]1[CH2:8][CH2:7][CH:6]([N:9]([CH3:36])[C:10](=[O:35])[CH2:11][CH2:12][C@H:13]([N:17]2[CH2:22][C:21]3[CH:23]=[C:24]([O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:25]=[CH:26][C:20]=3[N:19]=[C:18]2[NH2:34])[CH:14]([CH3:16])[CH3:15])[CH2:5][CH2:4]1)#[N:2].C[Si]([N:41]=[N+:42]=[N-:43])(C)C.C([Sn](=O)CCCC)CCC>COCCOC>[CH3:36][N:9]([CH:6]1[CH2:7][CH2:8][CH:3]([C:1]2[NH:43][N:42]=[N:41][N:2]=2)[CH2:4][CH2:5]1)[C:10](=[O:35])[CH2:11][CH2:12][C@H:13]([N:17]1[CH2:22][C:21]2[CH:23]=[C:24]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:25]=[CH:26][C:20]=2[N:19]=[C:18]1[NH2:34])[CH:14]([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 4-(S)-(2-amino-6-phenoxy-4H-pyrido[3,4-d]pyrimidin-3-yl)-5-methyl-hexanoic acid (4-cyano-cyclohexyl)-methyl-amide (0.26 g, 0.43 mmol) and trimethylsilylazide (0.17 mL, 1.29 mmol) in DME (1.5 mL) was added dibutyltin oxide (0.10 g, 0.40 mmol). The mixture was then heated in a microwave at 150° C. for 20 min. The solution was purified by HPLC to yield 4-(S)-(2-amino-6-phenoxy-4H-pyrido[3,4-d]pyrimidin-3-yl)-5-methyl-hexanoic acid methyl-[4-(1H-tetrazol-5-yl)-cyclohexyl]-amide as a white solid, as its corresponding trifluoroacetate salt.

Workup

customThe solution was purified by HPLC

Sources & evidence

ORD record: ord-65fd5269630949a49a41d80f4dd365a3
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531545B2

Reaction notes

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