Diisopropylethylamine → HCID 178451942, compound

HRID 1470949Notes

Reaction equation

HRID 1470949 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-c41a74773ccc409db373c4861e740241
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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