Potassium Iodide → HCID 178517859, compound

HRID 1044376Notes

Reaction equation

I[CH2:2][CH2:3][CH2:4][CH2:5]I.[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:31][CH2:30][CH2:29][C@@:16]3([C:20](=[O:21])[N:19]([C@H:22]4[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]4)[CH2:18][CH2:17]3)[CH2:15]2)=[C:10]([F:32])[CH:9]=1.O[C@H]1CC[C@H](N2CC[C@]3(CCCNC3)C2=O)CC1.[I-].[K+].C(O)(C(F)(F)F)=O>CN(C)C1C=CN=CC=1.CN(C=O)C.CO>[F:32][C:10]1[CH:9]=[C:8]([N:7]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:13]=[CH:12][C:11]=1[N:14]1[CH2:31][CH2:30][CH2:29][C@@:16]2([C:20](=[O:21])[N:19]([C@H:22]3[CH2:23][CH2:24][C@H:25]([OH:28])[CH2:26][CH2:27]3)[CH2:18][CH2:17]2)[CH2:15]1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 1,4-diiodobutane (13.5 μL, 0.000100 mol), (5S)-7-(4-amino-2-fluorophenyl)-2-(trans-4-hydroxycyclohexyl)-2,7-diazaspiro[4.5]decan-1-one (28.9 mg, 0.0000800 mol, this compound was prepared by using procedures analogous to that described for the synthesis of example 105, step 1 starting from (5S)-2-(trans-4-hydroxycyclohexyl)-2,7-diazaspiro[4.5]decan-1-one) and 4-dimethylaminopyridine (14.7 mg, 0.000120 mol) in DMF (1.00 mL), and potassium iodide (1.5 mg, 0.0000090 mol) was heated at 110° C. by microwave for 15 min. The mixture was diluted with methanol (0.8 mL) and was adjusted to be acidic with TFA (the pH was about 2.0). The resulting solution was purified by prep-HPLC to give the desired product. LC-MS: 416.2 (M+H)+.

Workup

customthis compound was prepared
customThe resulting solution was purified by prep-HPLC

Sources & evidence

ORD record: ord-fe7b9becf1574a94b0d0b7b7dd9cb5b2
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563570B2

Reaction notes

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