Diisopropylethylamine → HCID 178451942, compound

HRID 2364805Notes

Reaction equation

HRID 2364805 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=3)[CH:11]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[N:30]=[C:31]([C@@H:34]5[CH2:38][CH2:37][CH2:36][N:35]5[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[NH:32][CH:33]=4)=[CH:25][CH:24]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:46]([O:50][C:51]([N:53]1[CH2:57][CH2:56][CH2:55][C@H:54]1[C:58](O)=[O:59])=[O:52])([CH3:49])([CH3:48])[CH3:47].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CS(C)=O>[C:42]([O:41][C:39]([N:35]1[CH2:36][CH2:37][CH2:38][C@H:34]1[C:31]1[NH:32][CH:33]=[C:29]([C:26]2[CH:27]=[CH:28][C:23]([CH:11]3[N:12]([C:13]4[CH:18]=[CH:17][C:16]([C:19]([CH3:21])([CH3:22])[CH3:20])=[CH:15][CH:14]=4)[CH:8]([C:5]4[CH:4]=[CH:3][C:2]([NH:1][C:58]([C@H:54]5[CH2:55][CH2:56][CH2:57][N:53]5[C:51]([O:50][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:52])=[O:59])=[CH:7][CH:6]=4)[CH2:9][CH2:10]3)=[CH:24][CH:25]=2)[N:30]=1)=[O:40])([CH3:45])([CH3:44])[CH3:43]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178451914HCID 178451914, compound

Product 1

HCID 178451942HCID 178451942, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The product from Example 40D (1.3 g, 2.146 mmol), (S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (1.386 g, 6.44 mmol), HATU (1.305 g, 3.43 mmol) and Hunig's base (1.124 mL, 6.44 mmol) in DMSO (20 mL) was reacted according to the procedure in Example 39H to provide the title compound (1.01 g, 59%) as a mixture of stereoisomers.

Sources & evidence

ORD record
ord-c3f27dda003e4176873c61b0d2cab00e
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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