Triethylamine → HCID 86705764, compound

HRID 1054557Notes

Reaction equation

HRID 1054557 reaction equation
[C:1]([C:5]1[CH:50]=[CH:49][C:8]2[N:9]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][CH2:17][C@@H:18]3[C@H:22]4[O:23][C:24]([CH3:27])([CH3:26])[O:25][C@H:21]4[C@H:20]([N:28]4[C:32]5[N:33]=[CH:34][N:35]=[C:36]([NH:37][CH:38]6[CH2:40][CH2:39]6)[C:31]=5[CH:30]=[CH:29]4)[CH2:19]3)=[N:11][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:58][S:59](Cl)(=[O:61])=[O:60]>C(Cl)Cl>[CH:38]1([NH:37][C:36]2[C:31]3[CH:30]=[CH:29][N:28]([C@H:20]4[C@@H:21]5[O:25][C:24]([CH3:27])([CH3:26])[O:23][C@@H:22]5[C@@H:18]([CH2:17][N:16]([CH2:15][CH2:14][CH2:13][CH2:12][C:10]5[N:9]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[C:8]6[CH:49]=[CH:50][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:6][C:7]=6[N:11]=5)[S:59]([CH3:58])(=[O:61])=[O:60])[CH2:19]4)[C:32]=3[N:33]=[CH:34][N:35]=2)[CH2:40][CH2:39]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67818707HCID 67818707, compound

Product 1

HCID 86705764HCID 86705764, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-[(3aS,4R,6R,6aR)-6-({[4-(5-tert-Butyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl)butyl]amino}methyl)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-N-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.052 g, 0.074 mmol) was dissolved in dry DCM (1 ml) and dry Et3N (0.02 ml, 0.148 mmol) and methanesulfonyl chloride (0.01 ml, 0.089 mmol) was added dropwise at r.t. under N2. The reaction was left for 3 hrs after which time LCMS analysis showed the reaction had gone to −80% completion. The reaction was concentrated in vacuo and purified by UV directed prep HPLC to give the product as a white solid (0.028 g, 48%): MS (ESI+) for C40H61N7O5SSi m/z 391.3 [M+2H]2+, 780.1 [M+H]+; LC purity 83% (UV), 100% ELS (ret. time, 1.80 min); 1H NMR (500 MHz, CDCl3) δ 8.29 (s, 1H), 7.59-7.79 (m, 1H), 7.29-7.45 (m, 2H), 6.97 (d, J=3.63 Hz, 1H), 6.64 (br. s., 1H), 5.50 (s, 2H), 4.88-5.06 (m, 2H), 4.58 (br. s., 1H), 3.51-3.60 (m, 2H), 3.39-3.51 (m, 1H), 3.32 (br. s., 3H), 2.98 (br. s., 3H), 2.84-2.92 (m, 3H), 2.46 (br. s., 2H), 2.16 (d, J=11.66 Hz, 1H), 1.90-2.02 (m, 2H), 1.77-1.89 (m, 2H), 1.48-1.58 (m, 3H), 1.33-1.44 (m, 9H), 1.20-1.32 (m, 4H), 0.83-0.99 (m, 4H), 0.61-0.78 (m, 2H), −0.12-0.03 (m, 9H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by UV

Sources & evidence

ORD record
ord-7bacd23fa0ec4d9c9e7000affd885696
Source dataset
uspto-grants-2016_07
Patent number
US09394310B2

Reaction notes

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