Tert-Butylamine → HCID 178448978, compound

HRID 2200796Notes

Reaction equation

CS(O[CH2:6][C:7]1[CH:12]=[C:11]([O:13][C@H:14]2[CH2:19][CH2:18][C@@H:17]([N:20]3[CH2:23][C:22]([CH2:46][C:47]#[N:48])([N:24]4[CH:28]=[C:27]([C:29]5[C:30]6[CH:37]=[CH:36][N:35]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:45])([CH3:44])[CH3:43])[C:31]=6[N:32]=[CH:33][N:34]=5)[CH:26]=[N:25]4)[CH2:21]3)[CH2:16][CH2:15]2)[N:10]=[C:9]([C:49]([F:52])([F:51])[F:50])[N:8]=1)(=O)=O.[C:53]([NH2:57])([CH3:56])([CH3:55])[CH3:54].S([O-])(=O)(=O)C>C1COCC1>[C:53]([NH:57][CH2:6][C:7]1[N:8]=[C:9]([C:49]([F:52])([F:51])[F:50])[N:10]=[C:11]([O:13][C@@H:14]2[CH2:19][CH2:18][C@H:17]([N:20]3[CH2:23][C:22]([CH2:46][C:47]#[N:48])([N:24]4[CH:28]=[C:27]([C:29]5[C:30]6[CH:37]=[CH:36][N:35]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:43])([CH3:45])[CH3:44])[C:31]=6[N:32]=[CH:33][N:34]=5)[CH:26]=[N:25]4)[CH2:21]3)[CH2:16][CH2:15]2)[CH:12]=1)([CH3:56])([CH3:55])[CH3:54]

Participants

Conditions

Temperature: 50 °C

Procedure

[6-[(cis-4-{3-(Cyanomethyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}cyclohexyl)oxy]-2-(trifluoromethyl)pyrimidin-4-yl]methyl methanesulfonate (240 mg, 0.32 mmol) was dissolved in THF (2 mL), followed by addition of tert-butylamine (530 μL, 5.0 mmol). The flask was capped and heated in a 50° C. bath for 1 hour. LCMS and HPLC showed 92% conversion of the mesylate to product. HPLC showed the product to have UVmax 224, 250 and 308 nm. After another hour, the solvent was removed by rotary evaporation.

Workup

customThe flask was capped
waitAfter another hour
customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record: ord-efdc37f6681949deb863b554d67ebdc9
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359358B2

Reaction notes

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