Diisopropylethylamine → Hydrochloric Acid

HRID 1050510Notes

Reaction equation

HRID 1050510 reaction equation
[ClH:1].[N:2]1([C:8]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[N:18]=[C:19]([NH:26][C@@H:27]4[CH2:32][CH2:31][CH2:30][NH:29][CH2:28]4)[N:20]=[N:21][C:22]=3[C:23]([NH2:25])=[O:24])=[CH:12][CH:11]=2)=[O:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[CH3:33][N:34]([CH3:41])[CH2:35]/[CH:36]=[CH:37]/[C:38](O)=[O:39].CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN1C(=O)CCC1>[CH3:33][N:34]([CH3:41])[CH2:35]/[CH:36]=[CH:37]/[C:38]([N:29]1[CH2:30][CH2:31][CH2:32][C@@H:27]([NH:26][C:19]2[N:20]=[N:21][C:22]([C:23]([NH2:25])=[O:24])=[C:17]([NH:16][C:13]3[CH:14]=[CH:15][C:10]([C:8]([N:2]4[CH2:3][CH2:4][O:5][CH2:6][CH2:7]4)=[O:9])=[CH:11][CH:12]=3)[N:18]=2)[CH2:28]1)=[O:39].[ClH:1]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 14805664(2E)-4-(Dimethylamino)-2-butenoic acidHCID 118115258(R)-5-(4-(morpholine-4-carbonyl)phenylamino)-3-(piperidin-3-ylamino)-1,2,4-triazine-6-carboxamide HCl salt

Product 2

HCID 313Hydrochloric AcidYield 877.7%HCID 118114658US9656988, Example 66

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of (R)-5-(4-(morpholine-4-carbonyl)phenylamino)-3-(piperidin-3-ylamino)-1,2,4-triazine-6-carboxamide HCl salt (47 mg, 0.10 mmol) in NMP (4 mL) was added (E)-4-(dimethylamino)but-2-enoic acid (50 mg, 0.30 mmol), DIEA (180 μL, 1.0 mmol) and then PyBOP (104 mg, 0.20 mmol). The mixture was stirred at RT for 2 h, quenched with TFA (0.2 mL), diluted with 2 mL water, and subjected to reverse phase preparative HPLC to isolate the title compound (80) as an HCl salt (32 mg). MS found for C26H35N9O4 as (M+H)+ 538.2, (M−H)− 536.3. UV: λ=246 nm.

Workup

  1. customquenched with TFA (0.2 mL)
  2. additiondiluted with 2 mL water

Sources & evidence

ORD record
ord-e73d244c0fcd4451b3e64b072926db8f
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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